JP2011503155A - Sterilization mixture III - Google Patents

Abstract

［式中、R¹はH、C₁-C₆-アルキル、C₁-C₆-アルコキシ-C₁-C₆-アルキル、C₁-C₆-ハロアルキル、アリールまたはヘテロアリールであり、ここで最後の2個の基の環状部分は非置換であるか、またはハロゲン、C₁-C₄-アルキル、C₂-C₄-アルキニル、C₁-C₄-ハロアルキル、C₁-C₄-アルコキシ、C₁-C₄-アルキルチオ、C₁-C₄-ハロアルコキシ、シアノおよびニトロから選択される1、2または3個の基で置換され；Aは共有結合またはC₁-C₄-アルキレンであり、ここでC₁-C₄-アルキレンは非置換であるか、またはC₁-C₄-アルキル、C₁-C₄-ハロアルキル、C₁-C₄-アルコキシおよびシアノから選択される置換基をもつことができ；Arはアリールまたはヘテロアリールであり、ここで芳香族基の環状部分は非置換であるか、1、2または3個の基R^aで置換され、ここで基R^aは同一でも異なっていてもよく、ハロゲン、C₁-C₄-アルキル、C₂-C₄-アルケニル、C₂-C₄-アルキニル、C₁-C₄-ハロアルキル、C₁-C₄-アルコキシ、C₁-C₄-アルキルチオ、C₁-C₄-ハロアルコキシ、C₁-C₄-ハロアルキルチオ、シアノ、ニトロ、アリール、ヘタリール、アリールオキシ、ヘタリールオキシ、アリールオキシ-C₁-C₄-アルキルおよびヘタリールオキシ-C₁-C₄-アルキルから選択され、ここで最後に挙げた6個の基の環状部分は非置換であるか、またはハロゲン、C₁-C₄-アルキル、C₁-C₄-ハロアルキル、C₁-C₄-アルコキシ、C₁-C₄-アルキルチオ、C₁-C₄-ハロアルコキシ、シアノおよびニトロから選択される1、2または3個の基で置換される］またはその塩と、少なくとも1種のさらなる殺菌活性化合物IIとを含んでなる、殺菌活性化合物類の混合物に関する。
【選択図】 なしThe present invention provides at least one substituted 2- [hydroxyl (pyridin-3-yl) methyl] acrylate compound of formula (I):
[Chemical 1]

[Wherein R ¹ is H, C ₁ -C ₆ -alkyl, C ₁ -C ₆ -alkoxy-C ₁ -C ₆ -alkyl, C ₁ -C ₆ -haloalkyl, aryl or heteroaryl, wherein The cyclic part of the last two groups is unsubstituted or halogen, C ₁ -C ₄ -alkyl, C ₂ -C ₄ -alkynyl, C ₁ -C ₄ -haloalkyl, C ₁ -C ₄ -alkoxy Substituted with 1, 2 or 3 groups selected from C ₁ -C ₄ -alkylthio, C ₁ -C ₄ -haloalkoxy, cyano and nitro; A is a covalent bond or C ₁ -C ₄ -alkylene There, wherein C ₁ -C ₄ - alkylene is unsubstituted or C ₁ -C ₄ - alkyl, C ₁ -C ₄ - haloalkyl, C ₁ -C ₄ - substituents selected from alkoxy and cyano can have; Ar is aryl or heteroaryl, cyclic moiety wherein aromatic radicals are either unsubstituted, substituted with one, two or three groups R ^a, Kodemoto R ^a may be the same or different, halogen, C ₁ -C ₄ - alkyl, C ₂ -C ₄ - alkenyl, C ₂ -C ₄ - alkynyl, C ₁ -C ₄ - haloalkyl, C ₁ -C ₄ - alkoxy, C ₁ -C ₄ - alkylthio, C ₁ -C ₄ - haloalkoxy, C ₁ -C ₄ - haloalkylthio, cyano, nitro, aryl, hetaryl, aryloxy, hetaryl, aryloxy - Selected from C ₁ -C ₄ -alkyl and hetaryloxy-C ₁ -C ₄ -alkyl, wherein the cyclic groups of the last 6 groups mentioned are unsubstituted or halogen, C ₁ -C 1, 2 or 3 selected from ₄ -alkyl, C ₁ -C ₄ -haloalkyl, C ₁ -C ₄ -alkoxy, C ₁ -C ₄ -alkylthio, C ₁ -C ₄ -haloalkoxy, cyano and nitro Or a salt thereof and at least one further fungicidal active compound II, It relates to mixtures of the active compounds.
[Selection figure] None

Description

  The present invention relates to a mixture of fungicidal active compounds comprising at least one substituted 2- [hydroxyl (pyridin-3-yl) methyl] acrylic ester compound and at least one further fungicidal active compound.

  One typical problem that arises in the field of sterilization control is to allow effective control of pests while reducing or avoiding undesirable environmental or toxicological effects It is necessary to reduce the application rate of the active ingredient.

  Another problem faced is the need to make available fungicides effective against a wide range of fungi.

  Furthermore, there is a need for a bactericidal agent that combines knockdown activity and long-term control, i.e., combines rapid action and long-term action.

  A further problem that arises with the use of fungicides is that the repeated use of only individual fungicides often results in the rapid selection of harmful fungi that have acquired natural or adaptive resistance to the active compound. That is. Usually such strains are also cross-resistant to other active ingredients with the same mechanism of action. As a result, effective control of pathogenic bacteria by such active compounds can no longer be expected. However, development of an active ingredient having a new mechanism of action is difficult and expensive.

  Another problem underlying the present invention is the desire for a composition that improves plants, which improvement process is generally and hereinafter referred to as “plant health”. The term “plant health” includes improvements of various types of plants that are not related to fungal control. For example, advantageous properties that may be listed are improved crop characteristics including: emergence, yield, protein content, oil content, starch content, more developed root system (promoting root growth), stress tolerance Improved (eg resistance to drought, high temperature, salt, UV, water, low temperature), reduced ethylene (decreased production and / or reduced sensitivity), increased tillering, increased plant height, more Large leaf blades, reduced root mortality, more robust tillers, darker green leaves, pigment content, photosynthetic action, input required (fertilizer, water, etc.) Reduction, required seed reduction, more fertile tillers, early flowering, early grain maturation, reduced plant lodging, increased shoot growth, increased plant vitality, improved plant stand Good early germination, or others well known to those skilled in the art Advantageous properties.

  The object of the present invention is therefore the problem of reducing the application rate and / or the problem of enhancing the activity spectrum and / or the problem of combining knockdown activity with long term control and / or the problem of resistance management and / or plant health. It is to provide a sterilizing mixture that solves the problem of promoting.

  The inventors have surprisingly found that these objectives are specific bactericidal β-hydroxy-α-methylene-3-pyridinepropanoic acid esters of formula I as defined below (disclosed in WO2005 / 115148) In combination with certain other fungicidal active compounds II has been found to be achieved in part or in whole.

  In particular, a mixture of a compound of formula I as defined below and a compound II as defined below exhibits a markedly improved effect on fungi compared to the control rates that can be achieved by the individual compounds and / or It has been found to be suitable for improving plant health when applied to plants, plant parts, seeds or their habitat.

  It has been found that the action of the mixtures according to the invention far exceeds the fungicidal action and / or the plant health promoting action of the active compounds alone present in the mixture.

  In addition, the inventors have shown that simultaneous application of Compound I and Compound II (ie, together or separately) or sequential application of Compound I and Compound II is improved compared to the control rates that can be achieved with individual compounds. It was found to be possible to control harmful fungi (mixtures showing a synergistic effect).

Therefore, the present invention provides an active ingredient
1) At least one substituted 2- [hydroxyl (pyridin-3-yl) methyl] acrylate compound of formula I:

[Where:
R ¹ is H, C ₁ -C ₆ -alkyl, C ₁ -C ₆ -alkoxy-C ₁ -C ₆ -alkyl, C ₁ -C ₆ -haloalkyl, aryl or heteroaryl, where the last 2 The cyclic part of the groups is unsubstituted or halogen, C ₁ -C ₄ -alkyl, C ₂ -C ₄ -alkynyl, C ₁ -C ₄ -haloalkyl, C ₁ -C ₄ -alkoxy, C ₁ -C ₄ - alkylthio, C ₁ -C ₄ - haloalkoxy, substituted with one, two or three groups selected from cyano and nitro,
A is a covalent bond or C ₁ -C ₄ -alkylene, where C ₁ -C ₄ -alkylene is unsubstituted or C ₁ -C ₄ -alkyl, C ₁ -C ₄ -haloalkyl, C Can have a substituent selected from ₁ -C ₄ -alkoxy and cyano,
Ar is aryl or heteroaryl, wherein the cyclic portion of the aromatic group is unsubstituted or substituted with 1, 2, 3, 4 or 5 groups R ^a , where the groups R ^a are the same But may be different, halogen, C ₁ -C ₄ -alkyl, C ₂ -C ₄ -alkenyl, C ₂ -C ₄ -alkynyl, C ₁ -C ₄ -haloalkyl, C ₁ -C ₄ -alkoxy, C ₁ -C ₄ - alkylthio, C ₁ -C ₄ - haloalkoxy, C ₁ -C ₄ - haloalkylthio, cyano, nitro, aryl, hetaryl, aryloxy, hetaryl, aryloxy -C ₁ -C ₄ - alkyl And hetaryloxy-C ₁ -C ₄ -alkyl, wherein the cyclic part of the last six groups mentioned here is unsubstituted or halogen, C ₁ -C ₄ -alkyl, C _1- C ₄ -haloalkyl, C ₁ -C ₄ -alkoxy, C ₁ -C ₄ -alkylthio, C ₁ -C ₄ -haloalkoxy, cyano and nito Substituted with 1, 2 or 3 groups selected from
Or a salt thereof;
and
2) At least one fungicidal compound II selected from the following A) to F):
A) Azaconazole, dinicoazole-M (diniconazole-M), oxpoconazol, uniconazole, 1- (4-chloro-phenyl) -2-([1,2,4] triazole -1-yl) -cycloheptanol, imazalil sulfate, bitertanole, bromuconazole, cyproconazole, difenoconazole, diniconazole, enilconazole enilconazole), epoxiconazole, fenbuconazole, flusilazole, fluquinconazole, flutriafol, hexaconazole, imibenconazole, Ipconazole, metconazole, microbutanil, paclobutrazol, Penconazole, propiconazole, prothioconazole, simeconazole, tebuconazole, tetraconazole, uniconazole-P, triadimenol, triadimefon ), Triticonazole, cyazofamid, imazalyl, pefurazoate, prochloraz, triflumizol, benomyl, carbendazim, carbendazim, fuberidazole, (thiabendazole), ethaboxam, etridiazole, hymexazole, and 1- (4-chloro-phenyl) -1- (propyn-2-yloxy) -3- (4- (3,4- Selected from the group consisting of dimethoxy-phenyl) -isoxazol-5-yl) -propan-2-one Azole series;
B) 2- (2- (6- (3-Chloro-2-methyl-phenoxy) -5-fluoro-pyrimidin-4-yloxy) -phenyl) -2-methoxyimino-N-methyl-acetamide, 3-methoxy -2- (2- (N- (4-methoxy-phenyl) -cyclopropane-carboximidoylsulfanylmethyl) -phenyl) -acrylic acid methyl ester, azoxystrobin, dimoxystrobin , Enestroburin, fluoxastrobin, kresoxim-methyl, metinominostrobin, orysastrobin, picoxystrobin, pyraclostrobin ), Trifloxystrobin, methyl (2-chloro-5- [1- (3-methylbenzyloxyimino) ethyl] benzyl) carbamate, (2-chloro-5- [1- (6-methyl Pyridin-2-ylmethoxyi Roh) ethyl] benzyl) carbamate, and 2- (ortho - ((2,5-dimethylphenyl oxymethylene) phenyl) -3-strobilurin selected from the group consisting of methoxy methyl acrylate;
C) Benalaxyl-M, 2-amino-4-methyl-thiazole-5-carboxylic acid anilide, 2-chloro-N- (1,1,3-trimethyl-indan-4-yl) -nicotine Amide, N- (2- (1,3-Dimethylbutyl) -phenyl) -1,3-dimethyl-5-fluoro-1H-pyrazole-4-carboxylic acid amide, N- (4′-chloro-3 ′, 5-Difluoro-biphenyl-2-yl) -3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid amide, N- (4'-chloro-3 ', 5-difluoro-biphenyl-2-yl ) -3-Trifluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid amide, N- (3 ′, 4′-dichloro-5-fluoro-biphenyl-2-yl) -3-trifluoromethyl- 1-methyl-1H-pyrazole-4-carboxylic acid amide, N- (3 ′, 5-difluoro-4′-methyl-biphenyl-2-yl) -3-difluoromethyl-1-methyl-1H-pyrazole-4 -Carboxylic acid amide, N- (3 ', 5-difluoro-4'-methyl-biphenyl-2-yl) -3-tri Fluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid amide, N- (cis-2-bicyclopropyl-2-yl-phenyl) -3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid Acid amide, N- (trans-2-bicyclopropyl-2-yl-phenyl) -3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid amide, fluopyram, N- (3-ethyl -3,5,5-trimethyl-cyclohexyl) -3-formylamino-2-hydroxy-benzamide, oxytetracyclin, silthiofam, N- (6-methoxy-pyridin-3-yl) cyclopropanecarboxylic acid Acid amide, carboxin, benalaxyl, boscalid, fenhexamid, flutolanil, furametpyr, mepronil, metalaxyl, mefenoxam ,off Ofurace, oxadixyl, oxycarboxin, penthiopyrad, thifluzamide, tiadinil, N- (4'-bromobiphenyl-2-yl) -4-difluoromethyl -2-methylthiazole-5-carboxamide, N- (4'-trifluoromethylbiphenyl-2-yl) -4-difluoromethyl-2-methylthiazole-5-carboxamide, N- (4'-chloro-3 ' -Fluorobiphenyl-2-yl) -4-difluoromethyl-2-methylthiazole-5-carboxamide, N- (3 ', 4'-dichloro-4-fluorobiphenyl-2-yl) -3-difluoromethyl-1 -Methylpyrazole-4-carboxamide, N- (3 ', 4'-dichloro-5-fluorobiphenyl-2-yl) -3-difluoromethyl-1-methylpyrazole-4-carboxamide, 3,4-dichloro-N -(2-Cyanophenyl) isothiazole-5-carboxamide, N- (2 ', 4'-difluorobi Enyl-2-yl) -1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxamide, N- (2 ', 4'-dichlorobiphenyl-2-yl) -1-methyl-3-trifluoro Methyl-1H-pyrazole-4-carboxamide, N- (2 ′, 4′-difluorobiphenyl-2-yl) -3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide, N- (2 ′, 4'-dichlorobiphenyl-2-yl) -3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide, N- (2 ', 5'-difluorobiphenyl-2-yl) -1-methyl-3 -Trifluoromethyl-1H-pyrazole-4-carboxamide, N- (2 ', 5'-dichlorobiphenyl-2-yl) -1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxamide, N- (2 ', 5'-Difluorobiphenyl-2-yl) -3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide, N- (2', 5'-dichlorobiphenyl-2-yl) -3 -Difluoromethyl-1-methyl-1 H-pyrazole-4-carboxamide, N- (3 ′, 5′-difluorobiphenyl-2-yl) -1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxamide, N- (3 ′, 5 '-Dichlorobiphenyl-2-yl) -1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxamide, N- (3', 5'-difluorobiphenyl-2-yl) -3-difluoromethyl- 1-methyl-1H-pyrazole-4-carboxamide, N- (3 ′, 5′-dichlorobiphenyl-2-yl) -3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide, N- (3 '-Fluorobiphenyl-2-yl) -1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxamide, N- (3'-chlorobiphenyl-2-yl) -1-methyl-3-trifluoro Methyl-1H-pyrazole-4-carboxamide, N- (3′-fluorobiphenyl-2-yl) -3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide, N- (3′-chlorobiphenyl- 2- Yl) -3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide, N- (2'-fluorobiphenyl-2-yl) -1-methyl-3-trifluoromethyl-1H-pyrazole-4- Carboxamide, N- (2′-chlorobiphenyl-2-yl) -1-methyl-3-trifluoromethyl-1H-pyrazol-4-carboxamide, N- (2′-fluorobiphenyl-2-yl) -3- Difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide, N- (2′-chlorobiphenyl-2-yl) -3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide, N- (2 '-Fluoro-4'-chloro-5'-methylbiphenyl-2-yl) -1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxamide, N- (3', 4 ', 5'- Trifluorobiphenyl-2-yl) -1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxamide, N- (3 ′, 4 ′, 5′-trifluorobiphenyl-2-yl) -1- Methyl-3-difluoromethyl-1 H-pyrazole-4-carboxamide, N- (2 ′, 4 ′, 5′-trifluorobiphenyl-2-yl) -1-methyl-3-difluoromethyl-1H-pyrazole-4-carboxamide, N- (3 ', 4', 5'-trifluorobiphenyl-2-yl) -3-chlorofluoromethyl-1-methyl-1H-pyrazole-4-carboxamide, N- [2- (1,1,2,3,3 , 3-Hexafluoropropoxy) phenyl] -1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxamide, N- [2- (1,1,2,3,3,3-hexafluoropropoxy) -Phenyl] -3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide, N- [2- (2-chloro-1,1,2-trifluoroethoxy) phenyl] -1-methyl-3- Trifluoromethyl-1H-pyrazole-4-carboxamide, N- [2- (2-chloro-1,1,2-trifluoroethoxy) phenyl] -3-difluoromethyl-1-methyl-1H-pyrazole-4- Carboxamide, N- [2- (1,1,2,2-tetrafluoroethoxy) Enyl] -3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide, N- [2- (1,1,2,2-tetrafluoroethoxy) phenyl] -1-methyl-3-trifluoromethyl -1H-pyrazole-4-carboxamide, N- (4 '-(trifluoromethylthio) biphenyl-2-yl) -3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide, N- (4'- (Trifluoromethylthio) biphenyl-2-yl) -1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxamide, dimethomorph, flumorph, flumetover, fluopicolide (fluopicolide) Picobenzamid), zoxamide, carpropamid, diclocymet, mandipropamid, N- (2- {4- [3- (4-chlorophenyl) prop-2-ynyloxy] -3 -Methoxyphenyl} ethyl) -2-methanesulfonyla No-3-methylbutyramide and N- (2- {4- [3- (4-chlorophenyl) -prop-2-ynyloxy] -3-methoxyphenyl} ethyl) -2-ethanesulfonylamino-3-methyl A carboxamide system selected from the group consisting of butyramide;
D) 2,3,5,6-tetrachloro-4-methanesulfonyl-pyridine, 3,4,5-trichloropyridine-2,6-di-carbonitrile, N- (1- (5-bromo-3- Chloropyridin-2-yl) -ethyl) -2,4-dichloronicotinamide, N-[(5-bromo-3-chloropyridin-2-yl) -methyl] -2,4-dichloronicotinamide, diflumetrim ( diflumetorim, nitrapyrin, dodemorph acetate, fluoroimid, blasticidin-S (blasticidin-S), chinomethionat, debacarb, difenzoquat, difenzoquat, difenzoquat, difenzoquat, difenzoquat, difenzoquat Fenzoquat-methylsulfate, oxolinic acid, piperalin, fluazinam, pyrifenox, bupirimate, cyprodinil, fenarimol, ferimzone ), Mepanipyrim (mepanip yrim, nuarimol, pyrimethanil, triforine, fenpiclonil, fludioxonil, aldimorph, dodemorph, fenpropimorph, tridemorph, tridemorph Fenpropidin, iprodione, procymidone, vinclozolin, famoxadone, fenamidone, octhilinone, probenazole, amisulbrom (amisbrom) ), Diclomezine, pyroquilon, proquinazid, tricyclazole, 2-butoxy-6-iodo-3-propylchromen-4-one, acibenzolar-S-methyl ), Captafol, captan, dazomet (d azomet), folpet, phenoxanil, quinoxyfen, 3- [5- (4-chlorophenyl) -2,3-dimethylisoxazolidin-3-yl] pyridine, 5-chloro-7- (4-Methylpiperidin-1-yl) -6- (2,4,6-trifluorophenyl)-[1,2,4] triazolo [1,5-a] pyrimidine, 6- (3,4-dichlorophenyl ) -5-Methyl- [1,2,4] triazolo [1,5-a] pyrimidin-7-ylamine, 6- (4-tert-butylphenyl) -5-methyl- [1,2,4] triazolo [1,5-a] pyrimidin-7-ylamine, 5-methyl-6- (3,5,5-trimethylhexyl)-[1,2,4] triazolo [1,5-a] pyrimidin-7-ylamine 5-methyl-6-octyl- [1,2,4] triazolo [1,5-a] pyrimidin-7-ylamine, 6-methyl-5-octyl- [1,2,4] triazolo [1,5 -a] pyrimidin-7-ylamine, 6-ethyl-5-octyl- [1,2,4] triazolo [1,5-a] pyrimidin-7-ylamine, 5-ethyl-6-octyl- [1,2 , 4] bird Azolo [1,5-a] pyrimidin-7-ylamine, 5-ethyl-6- (3,5,5-trimethylhexyl)-[1,2,4] triazolo [1,5-a] pyrimidine-7- Ylamine, 6-octyl-5-propyl- [1,2,4] triazolo [1,5-a] pyrimidin-7-ylamine, 5-methoxymethyl-6-octyl- [1,2,4] triazolo [1 , 5-a] pyrimidin-7-ylamine, 6-octyl-5-trifluoromethyl- [1,2,4] triazolo [1,5-a] pyrimidin-7-ylamine, and 5-trifluoromethyl-6 A heterocyclic compound selected from the group consisting of-(3,5,5-trimethylhexyl)-[1,2,4] triazolo [1,5-a] pyrimidin-7-ylamine;
E) methasulphocarb, propamocarb hydrochlorid, mancozeb, maneb, metam, metyram, ferbam, propineb, thiram ), Zineb, ziram, thiophanate-methyl, dietofencarb, iprovalicarb, flubenthiavalicarb (benthiavalicarb), propamocarb (propamocarb), N- (1- (1- (4-cyanophenyl) ethanesulfonyl) -but-2-yl) carbamate 4-fluorophenyl, and 3- (4-chlorophenyl) -3- (2-iso A carbamate system selected from the group consisting of methyl propoxycarbonylamino-3-methylbutyrylamino) propanoate;
And
F) Guanidine series: dodine, iminoctadine, guazatine, dodin free base, guazatine-acetate, iminoctadine triacetate,
Antibiotic system: Kasugamycin, Streptomycin, Polyoxin, Validamycin A,
Nitrophenyl derivatives: binapacryl, dinocap, dinobuton,
Sulfur-containing heterocyclic compounds: dithianon, isoprothiolane,
Organometallic compounds: Fentine salts, such as fentin acetate,
Organophosphorus compounds: edifenphos, iprobenfos, fosetyl, fosetyl-aluminum, phosphorous acid and its salts, pyrazophos, tolclofos-methyl,
Organochlorine compounds: chlorothalonil, dichlofluanid, flusulfamide, hexachlorobenzene, phthalide, pencycuron, quintozene, tolylfluanid,
Inorganic active compounds: Bordeaux solution, copper acetate, copper hydroxide, copper oxychloride, basic copper sulfate, sulfur,
Others: cyflufenamid, cymoxanil, dimethirimol, etirimol, flaxaxyl, metrafenone, spiroxamine, iminoctadine-trisalbesylate (iminoctalbesilate) ), Kasugamycin hydrochloride hydrate, dichlorophen, pentachlorophenol and its salts, N- (4-chloro-2-nitro-phenyl) -N-ethyl-4-methyl-benzenesulfonamide, dichloran, nitrotar -Isopropyl, technazen, biphenyl, bronopol, diphenylamine, mildiomycin, oxine-copper, prohexadione calcium, N- (cyclopropylmethoxyimino- (6-difluoro-methoxy-2, 3-Difluoro-phenyl) -methyl) -2-phenylacetamide, N '-(4- (4 -Chloro-3-trifluoromethyl-phenoxy) -2,5-dimethyl-phenyl) -N-ethyl-N-methylformamidine, N '-(4- (4-fluoro-3-trifluoromethyl-phenoxy) -2,5-dimethyl-phenyl) -N-ethyl-N-methylformamidine, N '-(2-methyl-5-trifluoromethyl-4- (3-trimethylsilanyl-propoxy) -phenyl) -N -Ethyl-N-methylformamidine, and N '-(5-difluoromethyl-2-methyl-4- (3-trimethylsilanyl-propoxy) -phenyl) -N-ethyl-N-methylformamidine,
Other active compounds selected from the group consisting of:
In a synergistically effective relative amount.

  The invention also relates to a method for controlling harmful fungi using the mixtures according to the invention, the use of compounds I and active compounds II for preparing said mixtures and compositions comprising said mixtures.

  The present invention further relates to a mixture of plant protective active ingredients having a synergistically enhanced action for improving plant health, as well as a method for applying such a mixture of the invention to plants.

  The compounds described herein, and optionally all isomers thereof, can be used in the form of salts. Since some of the compounds I have basic centers, they can form, for example, acid addition salts. Acid addition salts include, for example, mineral acids (typically sulfuric acid, phosphoric acid, hydrohalic acid), organic carboxylic acids (typically acetic acid, oxalic acid, malonic acid, maleic acid, fumaric acid, phthalic acid). Acid), hydroxycarboxylic acid (typically ascorbic acid, lactic acid, malic acid, tartaric acid, citric acid), benzoic acid, or organic sulfonic acid (typically methanesulfonic acid, p-toluenesulfonic acid) Formed using. With at least one acidic group, the compounds of formula I can also form salts with bases. Salts with suitable bases are, for example, metal salts (typically alkali metal salts or alkaline earth metal salts, such as sodium, potassium, magnesium salts), or ammonia or organic amines (for example morpholine). , Piperidine, pyrrolidine, mono-, di- or trialkylamines, typically ethylamine, diethylamine, triethylamine or dimethylpropylamine, or mono-, di- or trihydroxyalkylamines, typically mono-, Di- or triethanolamine). Where appropriate, the formation of corresponding internal salts is also possible. Within the scope of the present invention, pesticide acceptable salts are preferred.

C _n -C _m represents the number of carbon atoms of each substituent or each part of the substituent.

  As used herein, “halo” or “halogen” refers to Cl, Br, I, or F.

  As used herein, “cyano” refers to a CN group.

  As used herein, “alkyl” refers to a saturated hydrocarbon group having 1 to 6 carbon atoms, particularly 1 to 4 carbon atoms, which may be linear or branched (eg, ethyl, isopropyl, t-amyl, or Hexyl). This definition applies both when the term alkyl is used alone or when it is used as part of a compound word, such as “haloalkyl”, “alkoxy”, “alkoxyalkyl”, “alkylthio”, and the like. apply. In certain embodiments, preferred alkyl groups are alkyl groups having 1 to 4 carbon atoms.

As used herein, “alkylene” refers to a linear divalent saturated hydrocarbon group. Or alkylene is unsubstituted or C ₁ -C _4, - alkyl, C ₁ -C ₄ - haloalkyl, C ₁ -C ₄ - may have a substituent selected from alkoxy and cyano. Representative examples of alkylene include, but are not limited to, methylene (CH ₂ ), 1,1-ethanediyl, 1,2-ethanediyl, 1,1-propanediyl, 1,2-propanediyl, 1, There may be mentioned 3-propanediyl, 1,1-butanediyl, 1,2-butanediyl, 1,3-butanediyl, 2,3-butanediyl or 1,4-butanediyl.

  As used herein, “haloalkyl” refers to an alkyl as defined herein in which part or all of the hydrogen atoms of the alkyl group are replaced by halogen atoms (particularly fluorine or chlorine atoms). Sure. Representative examples of haloalkyl include, but are not limited to, chloromethyl, 2-fluoroethyl, fluoromethyl, difluoromethyl, trifluoromethyl, 2,2,2-trifluoroethyl, pentafluoroethyl, and the like. It is done. This definition applies both when the term haloalkyl is used alone or when it is used as part of a compound word, such as “haloalkyloxy”, “haloalkylthio” and the like. In certain embodiments, preferred haloalkyl groups are those having 1 or 2 carbon atoms.

  As used herein, “alkenyl” refers to a straight or branched carbon chain having 2 to 6 carbon atoms containing at least one carbon-carbon double bond formed by removing two hydrogens. Point to a hydrogen group. Representative examples of “alkenyl” include, but are not limited to, ethenyl, 2-propenyl, 2-methyl-2-propenyl, 3-butenyl, 4-pentenyl, 5-hexenyl, and the like. As used herein, “lower alkenyl” is a small group of alkenyl and refers to a straight or branched hydrocarbon group having 2 to 4 carbon atoms.

  As used herein, “alkynyl” refers to a straight or branched hydrocarbon group of 2 to 6 carbon atoms containing at least one carbon-carbon triple bond. Representative examples of alkynyl include, but are not limited to, ethynyl, 1-propynyl, 2-propynyl, 3-butynyl, 2-pentynyl, 1-butynyl, and the like. As used herein, “lower alkynyl” is a small group of alkynyl and refers to a straight or branched hydrocarbon group having 2 to 4 carbon atoms.

  “Alkoxy” refers to an alkyl group, as defined above, attached to the remainder of the molecule through an oxygen atom (eg, methoxy, ethoxy and t-butoxy).

  As used herein, “alkylthio” refers to an alkyl group, as defined above, attached to the parent molecular moiety through a sulfur atom. Representative examples of alkylthio include, but are not limited to, methylthio, ethylthio, tert-butylthio, and the like.

  “Haloalkoxy” refers to a haloalkyl group as defined above attached to the remainder of the molecule through an oxygen atom (eg, 2-fluoroethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, 2, 2,2-trifluoroethoxy, pentafluoroethoxy, etc.).

  As used herein, “haloalkylthio” refers to a haloalkyl group as defined above attached to the parent molecular moiety through a sulfur atom. Representative examples of alkylthio include, but are not limited to, 2-fluoroethylthio, fluoromethylthio, difluoromethylthio, trifluoromethylthio, 2,2,2-trifluoroethylthio, pentafluoroethylthio, and the like. It is done.

  "Aryl" or "aromatic ring moiety" refers to an aromatic hydrocarbon substituent that can be a single ring or multiple rings, where the rings are fused together or covalently linked. Or linked to a common group such as an ethylene or methylene moiety. Representative examples of aryl include azulenyl, indanyl, indenyl, naphthyl, phenyl, tetrahydronaphthyl, biphenyl, diphenylmethyl, 2,2-diphenyl-1-ethyl, especially phenyl.

  “Aryloxy” refers to an aromatic hydrocarbon substituent as defined above attached to the remainder of the molecule through an oxygen atom. Representative examples of aryloxy include phenoxy, naphthyloxy, tetrahydronaphthyloxy, especially phenyloxy.

  “Heteroaryl” or “hetaryl” refers to a cyclic aromatic group in which one or more, for example 1, 2, 3 or 4, ring carbon atoms are replaced with heteroatoms such as O, S or N. means. If the heteroaryl group contains more than one heteroatom, the heteroatoms may be the same or different. Examples of heteroaryl groups include pyridyl, pyrimidinyl, imidazolyl, thienyl, furyl, pyrazinyl, pyrrolyl, benzofuranyl, isobenzofuranyl, chromenyl, xanthenyl, indolyl, isoindolyl, indolizinyl, triazolyl, pyridazinyl, indazolyl, quinolidinyl, isoquinolyl, quinolyl , Phthalazinyl, naphthyridinyl, quinoxalinyl, isothiazolyl, benzothiazolyl, pyrido [5,4-b] thiazolyl and benzo [b] thienyl. Preferred heteroaryl groups are 5- and 6-membered rings and contain 1-3 heteroatoms independently selected from O, N and S.

  “Hetaryloxy” refers to a hetaryl substituent as defined above attached to the remainder of the molecule through an oxygen atom. Representative examples of hetaryloxy include pyridyloxy, pyrimidinyloxy, thienyloxy, furyloxy and the like.

“Aryloxyalkyl” refers to an O-alkylene moiety (eg, O—CH ₂ , O—CH (CH ₃ ), O—CH ₂ CH ₂ , O—CH (CH ₃ ) CH _{2 in} the rest of the molecule. Or an O-CH ₂ —CH (CH ₃ ) — moiety) as defined above for an aromatic hydrocarbon substituent. Representative examples of aryloxyalkyl include phenoxymethyl, 1-phenoxyethyl, 2-phenoxyethyl, 1-phenoxypropyl, 2-phenoxypropyl and 1-methyl-2-phenoxyethyl.

“Hetaryloxyalkyl” refers to an O-alkylene moiety (eg, O—CH ₂ , O—CH (CH ₃ ), O—CH ₂ CH ₂ , O—CH (CH ₃ ) CH in the rest of the molecule. ₂ or O—CH ₂ —CH (CH ₃ ) — moiety) refers to a heteroaryl substituent as defined above. Representative examples of hetaryloxyalkyl include hetaryloxymethyl, 1-hetaryloxyethyl, 2-hetaryloxyethyl, 1-hetaryloxypropyl, 2-hetaryloxypropyl and 1-methyl-2 -Hetaryl oxyethyl is mentioned.

  “Agriculturally acceptable salt” means a salt known and recognized in the art for the cation of the salt to form an agricultural or horticultural salt. Preferably, the salt is water soluble.

Compounds of formula I in which R ¹ is different from hydrogen can exist in the form of E isomer IE and Z isomer IZ. In the mixtures of the present invention, compound I may exist as a pure E isomer or Z isomer, or as a mixture of E and Z isomers in any ratio.

In the compounds of formula I, the carbon atom with the hydroxyl group is the center of chirality. Thus, compounds of formula I can exist in the form of S enantiomer IS and R enantiomer IR. In the mixtures of the present invention, Compound I may exist as a pure S enantiomer or R enantiomer, or as a mixture of any ratio of S and R enantiomers.

Preferred compounds of formula I are those wherein R ¹ , A and Ar each independently or preferably in combination have one of the following meanings:
R ¹ is H, C ₁ -C ₆ -alkyl, phenyl or thienyl, wherein the cyclic part of said group is unsubstituted or halogen, C ₁ -C ₄ -alkyl, C ₂ -C ₄ Selected from -alkynyl, C ₁ -C ₄ -haloalkyl, C ₁ -C ₄ -alkoxy, C ₁ -C ₄ -alkylthio, C ₁ -C ₄ -haloalkoxy, cyano and nitro, in particular fluoro, chloro, methyl Substituted with 1, 2 or 3 groups selected from methoxy, difluoromethyl and trifluoromethyl. R ¹ is especially hydrogen, phenyl, 3-chlorophenyl, 4-chlorophenyl, 3-fluorophenyl, 4-fluorophenyl, 4-methoxyphenyl, 3,4-dichlorophenyl, 3,5-dichlorophenyl, 2,5-dichlorophenyl, 3 , 4-difluorophenyl, 3,5-difluorophenyl, 2,5-difluorophenyl, benzothien-2-yl, 2-thienyl, 5-chloro-2-thienyl, 3-methyl-2-thienyl, 5-methyl- Selected from 2-thienyl, 3-thienyl, 2-methyl-3-thienyl, 2-chloro-3-thienyl and 4-methyl-3-thienyl.

A is a covalent bond or especially CH ₂ ;
Ar is phenyl, which is unsubstituted or substituted with 1, 2 or 3 groups R ^a as defined above. R ^a is especially halogen, C ₁ -C ₄ -alkyl, C ₂ -C ₄ -alkenyl, C ₂ -C ₄ -alkynyl, C ₁ -C ₄ -haloalkyl, C ₁ -C ₄ -alkoxy, C ₁ -C Selected from ₄ -alkylthio, C ₁ -C ₄ -haloalkoxy, C ₁ -C ₄ -haloalkylthio, cyano, nitro, phenoxy and pyridyloxy, wherein the last two groups listed are unsubstituted Or selected from halogen, C ₁ -C ₄ -alkyl, C ₁ -C ₄ -haloalkyl, C ₁ -C ₄ -alkoxy, C ₁ -C ₄ -haloalkoxy, cyano and nitro, in particular fluoro, chloro, Substituted with 1, 2 or 3 groups selected from difluoromethyl and trifluoromethyl. Ar is selected in particular from phenyl having one or two groups selected from fluorine, chlorine, trifluoromethyl, methoxy, trifluoromethoxy, phenoxy and pyridyloxy, wherein the last two groups listed are non- It is substituted or substituted with 1 or 2 groups selected from fluorine, chlorine and trifluoromethyl. Examples of Ar include: phenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 2,4-dichlorophenyl, 2,3- Dichlorophenyl, 3,4-dichlorophenyl, 2,6-dichlorophenyl, 2-chloro-4-fluorophenyl, 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl, 2,4-difluorophenyl, 2,5-difluoro Phenyl, 3,5-difluorophenyl, 3,4-difluorophenyl, 3-chloro-4-fluorophenyl, 4-chloro-2-fluorophenyl, 2-chloro-5-trifluoromethylphenyl, 2-fluoro-4 -Trifluoromethylphenyl, 2-fluoro-5-trifluoromethylphenyl, 3-fluoro-5-trifluoromethylphenyl, 2-chloro-3-trifluoromethylphenyl, 4-fluoro-3-to Trifluoromethylphenyl, 4-chloro-3-trifluoromethylphenyl, 3-chloro-4-methylphenyl, 2-trifluoromethylphenyl, 3-trifluoromethylphenyl, 4-trifluoromethylphenyl, 3-methoxyphenyl 4-methoxyphenyl, 3-trifluoromethoxyphenyl, 4-trifluoromethoxyphenyl, 4-chloro-3,5-dimethylphenyl, 4-bromo-2,6-dimethylphenyl, 4- (4-chlorophenoxy) Phenyl, 4-phenoxyphenyl, 3- (5-chloropyridin-2-yl) oxyphenyl, 3- (5-trifluoromethylpyridin-2-yl) oxyphenyl, 4- (5-chloropyridin-2-yl) ) Oxyphenyl, 4- (5-trifluoromethylpyridin-2-yl) oxyphenyl, 3- (2-chloro-6-fluoro-4-trifluoromethylphenoxy) phenyl, 4- (2-chloro-6- Fluoro-4-trifluorome Ruphenoxy) phenyl, 3- (2,6-dichloro-4-trifluoromethylphenoxy) phenyl, 4- (2,6-dichloro-4-trifluoromethylphenoxy) phenyl, 2,3,4,5-tetra Fluorophenyl and pentafluorophenyl.

Particularly preferred embodiments of the present invention are compounds of formula I, wherein A and Ar are as defined above, having a particularly preferred meaning and R ¹ has ^one of the following meanings, tautomerism thereof For mixtures containing body or salt:
R ¹ is hydrogen or C ₁ -C ₆ -alkyl, especially hydrogen.

Another particularly preferred embodiment of the present invention is a compound of formula I, wherein A and Ar are as defined above, in particular having a preferred meaning and R ¹ has ^one of the following meanings: For mixtures containing mutants or salts:
R ¹ is phenyl or thienyl, wherein the cyclic part of said group is unsubstituted or halogen, C ₁ -C ₄ -alkyl, C ₂ -C ₄ -alkynyl, C ₁ -C ₄ -haloalkyl C ₁ -C ₄ -alkoxy, C ₁ -C ₄ -alkylthio, C ₁ -C ₄ -haloalkoxy, cyano and nitro, especially from fluoro, chloro, methyl, methoxy, difluoromethyl and trifluoromethyl Substituted with 1, 2 or 3 groups selected. R ¹ is especially hydrogen, phenyl, 3-chlorophenyl, 4-chlorophenyl, 3-fluorophenyl, 4-fluorophenyl, 4-methoxyphenyl, 3,4-dichlorophenyl, 3,5-dichlorophenyl, 2,5-dichlorophenyl, 3 , 4-difluorophenyl, 3,5-difluorophenyl, 2,5-difluorophenyl, benzothien-2-yl, 2-thienyl, 5-chloro-2-thienyl, 3-methyl-2-thienyl, 5-methyl- Selected from 2-thienyl, 3-thienyl, 2-methyl-3-thienyl, 2-chloro-3-thienyl and 4-methyl-3-thienyl.

A particularly preferred embodiment of the present invention relates to mixtures containing compounds of formula I, tautomers or salts thereof, wherein R ¹ , A and Ar have the following meanings:
R ¹ is hydrogen;
A is a covalent bond or especially CH ₂ and
Ar is phenyl, which is unsubstituted or substituted with 1, 2 or 3 groups R ^a as defined above. R ^a is especially halogen, C ₁ -C ₄ -alkyl, C ₂ -C ₄ -alkenyl, C ₂ -C ₄ -alkynyl, C ₁ -C ₄ -haloalkyl, C ₁ -C ₄ -alkoxy, C ₁ -C Selected from ₄ -alkylthio, C ₁ -C ₄ -haloalkoxy, C ₁ -C ₄ -haloalkylthio, cyano, nitro, phenoxy and pyridyloxy, wherein the last two groups listed are unsubstituted Or selected from halogen, C ₁ -C ₄ -alkyl, C ₁ -C ₄ -haloalkyl, C ₁ -C ₄ -alkoxy, C ₁ -C ₄ -haloalkoxy, cyano and nitro, in particular fluoro, chloro, Substituted with 1, 2 or 3 groups selected from difluoromethyl and trifluoromethyl. Ar is selected in particular from phenyl having one or two groups selected from fluorine, chlorine, trifluoromethyl, methoxy, trifluoromethoxy, phenoxy and pyridyloxy, wherein the last two groups listed are non- It is substituted or substituted with 1 or 2 groups selected from fluorine, chlorine and trifluoromethyl. Examples of Ar include: phenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 2,4-dichlorophenyl, 2,3- Dichlorophenyl, 3,4-dichlorophenyl, 2,6-dichlorophenyl, 2-chloro-4-fluorophenyl, 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl, 2,4-difluorophenyl, 2,5-difluoro Phenyl, 3,5-difluorophenyl, 3,4-difluorophenyl, 3-chloro-4-fluorophenyl, 4-chloro-2-fluorophenyl, 2-chloro-5-trifluoromethylphenyl, 2-fluoro-4 -Trifluoromethylphenyl, 2-fluoro-5-trifluoromethylphenyl, 3-fluoro-5-trifluoromethylphenyl, 2-chloro-3-trifluoromethylphenyl, 4-fluoro-3-to Trifluoromethylphenyl, 4-chloro-3-trifluoromethylphenyl, 3-chloro-4-methylphenyl, 2-trifluoromethylphenyl, 3-trifluoromethylphenyl, 4-trifluoromethylphenyl, 3-methoxyphenyl 4-methoxyphenyl, 3-trifluoromethoxyphenyl, 4-trifluoromethoxyphenyl, 4-chloro-3,5-dimethylphenyl, 4-bromo-2,6-dimethylphenyl, 4- (4-chlorophenoxy) Phenyl, 4-phenoxyphenyl, 3- (5-chloropyridin-2-yl) oxyphenyl, 3- (5-trifluoromethylpyridin-2-yl) oxyphenyl, 4- (5-chloropyridin-2-yl) ) Oxyphenyl, 4- (5-trifluoromethylpyridin-2-yl) oxyphenyl, 3- (2-chloro-6-fluoro-4-trifluoromethylphenoxy) phenyl, 4- (2-chloro-6- Fluoro-4-trifluorome Ruphenoxy) phenyl, 3- (2,6-dichloro-4-trifluoromethylphenoxy) phenyl, 4- (2,6-dichloro-4-trifluoromethylphenoxy) phenyl, 2,3,4,5-tetra Fluorophenyl and pentafluorophenyl.

Another particularly preferred embodiment of the present invention relates to mixtures containing compounds of formula I, tautomers or salts thereof, wherein R ¹ , A and Ar have the following meanings:
R ¹ is phenyl or thienyl, wherein the cyclic part of said group is unsubstituted or halogen, C ₁ -C ₄ -alkyl, C ₂ -C ₄ -alkynyl, C ₁ -C ₄ -haloalkyl C ₁ -C ₄ -alkoxy, C ₁ -C ₄ -alkylthio, C ₁ -C ₄ -haloalkoxy, cyano and nitro, especially from fluoro, chloro, methyl, methoxy, difluoromethyl and trifluoromethyl Substituted with 1, 2 or 3 groups selected. R ¹ is especially hydrogen, phenyl, 3-chlorophenyl, 4-chlorophenyl, 3-fluorophenyl, 4-fluorophenyl, 4-methoxyphenyl, 3,4-dichlorophenyl, 3,5-dichlorophenyl, 2,5-dichlorophenyl, 3 , 4-difluorophenyl, 3,5-difluorophenyl, 2,5-difluorophenyl, benzothien-2-yl, 2-thienyl, 5-chloro-2-thienyl, 3-methyl-2-thienyl, 5-methyl- Selected from 2-thienyl, 3-thienyl, 2-methyl-3-thienyl, 2-chloro-3-thienyl and 4-methyl-3-thienyl;
A is a covalent bond or especially CH ₂ and
Ar is phenyl, which is unsubstituted or substituted with 1, 2 or 3 groups R ^a as defined above. R ^a is especially halogen, C ₁ -C ₄ -alkyl, C ₂ -C ₄ -alkenyl, C ₂ -C ₄ -alkynyl, C ₁ -C ₄ -haloalkyl, C ₁ -C ₄ -alkoxy, C ₁ -C Selected from ₄ -alkylthio, C ₁ -C ₄ -haloalkoxy, C ₁ -C ₄ -haloalkylthio, cyano, nitro, phenoxy and pyridyloxy, wherein the last two groups listed are unsubstituted Or selected from halogen, C ₁ -C ₄ -alkyl, C ₁ -C ₄ -haloalkyl, C ₁ -C ₄ -alkoxy, C ₁ -C ₄ -haloalkoxy, cyano and nitro, in particular fluoro, chloro, Substituted with 1, 2 or 3 groups selected from difluoromethyl and trifluoromethyl. Ar is selected in particular from phenyl having one or two groups selected from fluorine, chlorine, trifluoromethyl, methoxy, trifluoromethoxy, phenoxy and pyridyloxy, wherein the last two groups listed are non- It is substituted or substituted with 1 or 2 groups selected from fluorine, chlorine and trifluoromethyl. Examples of Ar include: phenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 2,4-dichlorophenyl, 2,3- Dichlorophenyl, 3,4-dichlorophenyl, 2,6-dichlorophenyl, 2-chloro-4-fluorophenyl, 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl, 2,4-difluorophenyl, 2,5-difluoro Phenyl, 3,5-difluorophenyl, 3,4-difluorophenyl, 3-chloro-4-fluorophenyl, 4-chloro-2-fluorophenyl, 2-chloro-5-trifluoromethylphenyl, 2-fluoro-4 -Trifluoromethylphenyl, 2-fluoro-5-trifluoromethylphenyl, 3-fluoro-5-trifluoromethylphenyl, 2-chloro-3-trifluoromethylphenyl, 4-fluoro-3-to Trifluoromethylphenyl, 4-chloro-3-trifluoromethylphenyl, 3-chloro-4-methylphenyl, 2-trifluoromethylphenyl, 3-trifluoromethylphenyl, 4-trifluoromethylphenyl, 3-methoxyphenyl 4-methoxyphenyl, 3-trifluoromethoxyphenyl, 4-trifluoromethoxyphenyl, 4-chloro-3,5-dimethylphenyl, 4-bromo-2,6-dimethylphenyl, 4- (4-chlorophenoxy) Phenyl, 4-phenoxyphenyl, 3- (5-chloropyridin-2-yl) oxyphenyl, 3- (5-trifluoromethylpyridin-2-yl) oxyphenyl, 4- (5-chloropyridin-2-yl) ) Oxyphenyl, 4- (5-trifluoromethylpyridin-2-yl) oxyphenyl, 3- (2-chloro-6-fluoro-4-trifluoromethylphenoxy) phenyl, 4- (2-chloro-6- Fluoro-4-trifluorome Ruphenoxy) phenyl, 3- (2,6-dichloro-4-trifluoromethylphenoxy) phenyl, 4- (2,6-dichloro-4-trifluoromethylphenoxy) phenyl, 2,3,4,5-tetra Fluorophenyl and pentafluorophenyl.

Examples of compounds of the present invention include, but are not limited to, the following compounds I.1-I.73 listed in Table A:
Table A
I.1 2- [Hydroxyl (pyridin-3-yl) methyl] acrylic acid (3-trifluoromethylphenyl) methyl;
I.2 2- [Hydroxyl (pyridin-3-yl) methyl] acrylic acid (4-trifluoromethylphenyl) methyl;
I.3 2- [Hydroxyl (pyridin-3-yl) methyl] -3-phenylacrylic acid (3-trifluoromethylphenyl) methyl;
I.4 2- [Hydroxyl (pyridin-3-yl) methyl] -3-phenylacrylic acid (4-chloro-3-trifluoromethylphenyl) methyl;
I.5 2- [Hydroxyl (pyridin-3-yl) methyl] -3- (4-chlorophenyl) acrylic acid (3-trifluoromethylphenyl) methyl;
I.6 2- [Hydroxyl (pyridin-3-yl) methyl] -3- (2-chlorophenyl) acrylic acid (3-trifluoromethylphenyl) methyl;
I.7 2- [Hydroxyl (pyridin-3-yl) methyl] -3- (3-chlorophenyl) acrylic acid (3-trifluoromethylphenyl) methyl;
I.8 2- [Hydroxyl (pyridin-3-yl) methyl] -3- (4-fluorophenyl) acrylic acid (3-trifluoromethylphenyl) methyl;
I.9 2- [Hydroxyl (pyridin-3-yl) methyl] -3- (2-fluorophenyl) acrylic acid (3-trifluoromethylphenyl) methyl;
I.10 2- [Hydroxyl (pyridin-3-yl) methyl] -3- (3-fluorophenyl) acrylic acid (3-trifluoromethylphenyl) methyl;
I.11 2- [Hydroxyl (pyridin-3-yl) methyl] -3- (3,4-difluorophenyl) acrylic acid (3-trifluoromethylphenyl) methyl;
I.12 2- [Hydroxyl (pyridin-3-yl) methyl] -3- (3,5-difluorophenyl) acrylic acid (3-trifluoromethylphenyl) methyl;
I.13 2- [Hydroxyl (pyridin-3-yl) methyl] -3- (2,5-difluorophenyl) acrylic acid (3-trifluoromethylphenyl) methyl;
I.14 2- [Hydroxyl (pyridin-3-yl) methyl] -3- (3,4-dichlorophenyl) acrylic acid (3-trifluoromethylphenyl) methyl;
I.15 2- [Hydroxyl (pyridin-3-yl) methyl] -3- (3,5-dichlorophenyl) acrylic acid (3-trifluoromethylphenyl) methyl;
I.16 2- [Hydroxyl (pyridin-3-yl) methyl] -3- (2,5-dichlorophenyl) acrylic acid (3-trifluoromethylphenyl) methyl;
I.17 2- [Hydroxyl (pyridin-3-yl) methyl] -3- (4-methoxyphenyl) acrylic acid (3-trifluoromethylphenyl) methyl;
I.18 2- [Hydroxyl (pyridin-3-yl) methyl] -3- (3-thienyl) acrylic acid (3-trifluoromethylphenyl) methyl;
I.19 2- [Hydroxyl (pyridin-3-yl) methyl] -3- (2-thienyl) acrylic acid (3-trifluoromethylphenyl) methyl;
I.20 2- [Hydroxyl (pyridin-3-yl) methyl] -3- (5-chloro-2-thienyl) acrylic acid (3-trifluoromethylphenyl) methyl;
I.21 2- [Hydroxyl (pyridin-3-yl) methyl] -3- (5-methyl-2-thienyl) acrylic acid (3-trifluoromethylphenyl) methyl;
I.22 2- [Hydroxyl (pyridin-3-yl) methyl] -3- (3-methyl-2-thienyl) acrylic acid (3-trifluoromethylphenyl) methyl;
I.23 2- [Hydroxyl (pyridin-3-yl) methyl] -3- (4-methyl-3-thienyl) acrylic acid (3-trifluoromethylphenyl) methyl;
I.24 2- [Hydroxyl (pyridin-3-yl) methyl] -3- (5-methyl-3-thienyl) acrylic acid (3-trifluoromethylphenyl) methyl;
I.25 2- [Hydroxyl (pyridin-3-yl) methyl] -3- (2-chloro-3-thienyl) acrylic acid (3-trifluoromethylphenyl) methyl;
I.26 2- [hydroxyl (pyridin-3-yl) methyl] -acrylic acid (3-trifluoromethoxyphenyl) methyl;
I.27 2- [Hydroxyl (pyridin-3-yl) methyl] -acrylic acid (4-trifluoromethoxyphenyl) methyl;
I.28 2- [Hydroxyl (pyridin-3-yl) methyl] -acrylic acid (4-chloro-3-trifluoromethylphenyl) methyl;
I.29 2- [Hydroxyl (pyridin-3-yl) methyl] -acrylic acid (3,4-dichlorophenyl) methyl;
I.30 2- [Hydroxyl (pyridin-3-yl) methyl] -3- (3-thienyl) acrylic acid (2,6-dichlorophenyl) methyl;
I.31 2- [Hydroxyl (pyridin-3-yl) methyl] -3- (3-thienyl) acrylic acid (2-chloro-3-trifluoromethylphenyl) methyl;
I.32 2- [Hydroxyl (pyridin-3-yl) methyl] -3- (3-thienyl) acrylic acid (2-fluoro-3-trifluoromethylphenyl) methyl;
I.33 2- [Hydroxyl (pyridin-3-yl) methyl] -3- (3-thienyl) acrylic acid (3-chloro-4-methylphenyl) methyl;
I.34 2- [Hydroxyl (pyridin-3-yl) methyl] acrylic acid 1- (3-trifluoromethylphenyl) propyl;
I.35 2- [Hydroxyl (pyridin-3-yl) methyl] acrylic acid 2- (3-trifluoromethylphenyl) -1-methylethyl;
I.36 2- [Hydroxyl (pyridin-3-yl) methyl] acrylic acid 1- (3-trifluoromethylphenyl) ethyl;
I.37 2- [Hydroxyl (pyridin-3-yl) methyl] acrylic acid 2- (3-trifluoromethylphenyl) ethyl;
I.38 1- (2-Phenylphenyl) ethyl 2- [hydroxyl (pyridin-3-yl) methyl] acrylate;
I.39 2- [Hydroxyl (pyridin-3-yl) methyl] -acrylic acid 2- (4-chlorophenyl) ethyl;
I.40 2- [Hydroxyl (pyridin-3-yl) methyl] -acrylic acid 2- (3-chlorophenyl) ethyl;
I.41 2- [Hydroxyl (pyridin-3-yl) methyl] acrylic acid 4- (4-chlorophenoxy) phenylmethyl;
I.42 2- [Hydroxyl (pyridin-3-yl) methyl] acrylic acid 4- (3-chlorophenoxy) phenylmethyl;
I.43 2- [Hydroxyl (pyridin-3-yl) methyl] acrylic acid 4-phenoxyphenylmethyl;
I.44 2- [Hydroxyl (pyridin-3-yl) methyl] acrylic acid 3- (5-chloropyridin-2-yloxy) phenylmethyl;
I.45 2- [Hydroxyl (pyridin-3-yl) methyl] acrylic acid 4- (5-chloropyridin-2-yloxy) phenylmethyl;
I.46 2- [Hydroxyl (pyridin-3-yl) methyl] acrylic acid 3- (5-trifluoromethylpyridin-2-yloxy) phenylmethyl;
I.47 2- [Hydroxyl (pyridin-3-yl) methyl] acrylic acid 4- (5-trifluoromethylpyridin-2-yloxy) phenylmethyl;
I.48 2- [Hydroxyl (pyridin-3-yl) methyl] acrylic acid 3- (2-chloro-6-fluoro-4-trifluoromethylphenoxy) phenylmethyl;
I.49 2- [Hydroxyl (pyridin-3-yl) methyl] acrylic acid 4- (2-chloro-6-fluoro-4-trifluoromethylphenoxy) phenylmethyl;
I.50 2- [Hydroxyl (pyridin-3-yl) methyl] acrylic acid 3- (2,6-dichloro-4-trifluoromethylphenoxy) phenylmethyl;
I.51 2- [Hydroxyl (pyridin-3-yl) methyl] acrylic acid 4- (2,6-dichloro-4-trifluoromethylphenoxy) phenylmethyl;
I.52 2- [Hydroxyl (pyridin-3-yl) methyl] acrylate 4-chlorophenyl;
I.53 2- [Hydroxyl (pyridin-3-yl) methyl] acrylic acid 3-chlorophenyl;
I.54 2- [Hydroxyl (pyridin-3-yl) methyl] 2-chlorophenyl acrylate;
I.55 2- [Hydroxyl (pyridin-3-yl) methyl] acrylic acid 4-fluorophenyl;
I.56 2- [Hydroxyl (pyridin-3-yl) methyl] acrylic acid 3-trifluoromethylphenyl;
I.57 2- [Hydroxyl (pyridin-3-yl) methyl] acrylic acid 2,3-dichlorophenyl;
I.58 2- [Hydroxyl (pyridin-3-yl) methyl] acrylic acid 2,4-dichlorophenyl;
I.59 2- [Hydroxyl (pyridin-3-yl) methyl] acrylic acid 2,6-dichlorophenyl;
I.60 2- [Hydroxyl (pyridin-3-yl) methyl] acrylic acid 3,4-dichlorophenyl;
I.61 2- [Hydroxyl (pyridin-3-yl) methyl] acrylic acid 2,3-difluorophenyl;
I.62 2- [Hydroxyl (pyridin-3-yl) methyl] acrylic acid 2,4-difluorophenyl;
I.63 2- [Hydroxyl (pyridin-3-yl) methyl] acrylic acid 3,4-difluorophenyl;
I.64 2- [Hydroxyl (pyridin-3-yl) methyl] acrylic acid 2,6-difluorophenyl;
I.65 2- [Hydroxyl (pyridin-3-yl) methyl] acrylic acid 2,5-difluorophenyl;
I.66 2- [Hydroxyl (pyridin-3-yl) methyl] acrylic acid 4-chloro-3-fluorophenyl;
I.67 2- [Hydroxyl (pyridin-3-yl) methyl] acrylic acid 4-chloro-2-fluorophenyl;
I.68 2- [Hydroxyl (pyridin-3-yl) methyl] acrylic acid 4-methoxyphenyl;
I.69 2- [Hydroxyl (pyridin-3-yl) methyl] acrylic acid 4-phenoxyphenyl;
I.70 2- [Hydroxyl (pyridin-3-yl) methyl] acrylic acid 4-methylphenyl;
I.71 2- [Hydroxyl (pyridin-3-yl) methyl] acrylic acid 3- (5-chloropyridin-2-yloxy) phenylmethyl;
I.72 2- [Hydroxyl (pyridin-3-yl) methyl] acrylic acid 3- (5-trifluoromethylpyridin-2-yloxy) phenylmethyl;
I.73 2- [Hydroxyl (pyridin-3-yl) methyl] acrylic acid 4- (5-trifluoromethylpyridin-2-yloxy) phenylmethyl;
And their salts.

  Of the compounds listed in Table A, preferred are compounds I.1 to I.40, and more preferred are compounds I.1 to I.33. Particularly preferred are mixtures in which compound I is selected from compounds I.1 and I.3.

The active compounds II mentioned above, their preparation and their action against harmful fungi are generally known (see http://www.hclrss.demon.co.uk/index.html); they are commercially available ing. In particular, they are known from the following documents:
Vitertanol, β-([1,1′-biphenyl] -4-yloxy) -α- (1,1-dimethylethyl) -1H-1,2,4-triazole-1-ethanol (DE 23 24 020);
Bromuconazole, 1-[[4-Bromo-2- (2,4-dichlorophenyl) tetrahydro-2-furanyl] methyl] -1H-1,2,4-triazole (Proc. 1990 Br. Crop. Prot. Conf -Pests Dis. Vol. 1, p. 459);
Cyproconazole, 2- (4-chlorophenyl) -3-cyclopropyl-1- [1,2,4] triazol-1-ylbutan-2-ol (US 4 664 696);
Diphenoconazole, 1- {2- [2-chloro-4- (4-chlorophenoxy) phenyl] -4-methyl- [1,3] dioxolan-2-ylmethyl} -1H- [1,2,4] triazole ( GB-A 2 098 607);
Diniconazole, (βE) -β-[(2,4-Dichlorophenyl) methylene] -α- (1,1-dimethylethyl) -1H-1,2,4-triazole-1-ethanol (Noyaku Kagaku, 1983, Vol. 8, p. 575);
Enilconazole (imazalyl), 1- [2- (2,4-dichlorophenyl) -2- (2-propenyloxy) ethyl] -1H-imidazole (Fruits, 1973, Vol. 28, p. 545);
Epoxyconazole, (2RS, 3SR) -1- [3- (2-chlorophenyl) -2,3-epoxy-2- (4-fluorophenyl) propyl] -1H-1,2,4-triazole (EP- A 196 038);
Fluquinconazole, 3- (2,4-dichlorophenyl) -6-fluoro-2- [1,2,4] -triazol-1-yl-3H-quinazolin-4-one (Proc. Br. Crop Prot. Conf .-Pests Dis., 5-3, 411 (1992));
Fenbuconazole, α- [2- (4-chlorophenyl) ethyl] -α-phenyl-1H-1,2,4-triazole-1-propanenitrile (Proc. 1988 Br. Crop Prot. Conf.-Pests Dis. Vol. 1, p. 33);
Flucilazole, 1-{[bis- (4-fluorophenyl) methylsilanyl] methyl} -1H- [1,2,4] triazole (Proc. Br. Crop Prot. Conf.-Pests Dis., 1, 413 (1984) );
Flutriahole, α- (2-fluorophenyl) -α- (4-fluorophenyl) -1H-1,2,4-triazole-1-ethanol (EP 15 756);
Hexaconazole, 2- (2,4-dichlorophenyl) -1- [1,2,4] triazol-1-ylhexan-2-ol (CAS RN 79983-71-4);
Imibenconazole, N- (2,4-dichlorophenyl) -1H-1,2,4-triazole-1-ethaneimidothioate (4-chlorophenyl) methyl (Proc. 1988 Br. Crop Prot. Conf.-Pests Dis. Vol 2, p. 519);
Imidothioate (Proc. 1988 Br. Crop Prot. Conf.- Pests Dis. Vol. 2, p. 519);
Ipconazole, 2-[(4-chlorophenyl) methyl] -5- (1-methylethyl) -1- (1H-1,2,4-triazol-1-ylmethyl) cyclopentanol (EP 267 778);
Metconazole, 5- (4-chlorobenzyl) -2,2-dimethyl-1- [1,2,4] triazol-1-ylmethylcyclopentanol (GB 857 383);
Microbutanyl, 2- (4-chlorophenyl) -2- [1,2,4] triazol-1-ylmethylpentanenitrile (CAS RN 88671-89-0);
Penconazole, 1- [2- (2,4-dichlorophenyl) pentyl] -1H- [1,2,4] triazole (Pesticide Manual, 12th edition (2000), p.712);
Propiconazole, 1-[[2- (2,4-dichlorophenyl) -4-propyl-1,3-dioxolan-2-yl] methyl] -1H-1,2,4-triazole (BE 835 579);
Prothioconazole, 2- [2- (1-chlorocyclopropyl) -3- (2-chlorophenyl) -2-hydroxypropyl] -2,4-dihydro- [1,2,4] triazole-3-thione ( WO 96/16048);
Cimeconazole, α- (4-fluorophenyl) -α-[(trimethylsilyl) methyl] -1H-1,2,4-triazole-1-ethanol [CAS RN 149508-90-7];
Triazimephone, 1- (4-chlorophenoxy) -3,3-dimethyl-1- (1H-1,2,4-triazol-1-yl) -2-butanone;
Triadimenol, β- (4-chlorophenoxy) -α- (1,1-dimethylethyl) -1H-1,2,4-triazole-1-ethanol;
Tebuconazole, 1- (4-chlorophenyl) -4,4-dimethyl-3- [1,2,4] triazol-1-ylmethylpentan-3-ol (EP-A 40 345);
Tetraconazole, 1- [2- (2,4-dichlorophenyl) -3- (1,1,2,2-tetrafluoroethoxy) propyl] -1H-1,2,4-triazole (EP 234 242);
Triticonazole, (5E) -5-[(4-chlorophenyl) methylene] -2,2-dimethyl-1- (1H-1,2,4-triazol-1-ylmethyl) cyclopentanol (FR 26 41 277 );
Prochloraz, N- {propyl- [2- (2,4,6-trichlorophenoxy) ethyl]} imidazole-1-carboxamide (US 3 991 071);
Pefurazoate, 2-[(2-furanylmethyl) (1H-imidazol-1-ylcarbonyl) amino] butanoic acid 4-pentenyl [CAS RN 101903-30-4];
Triflumizole, (4-chloro-2-trifluoromethylphenyl)-(2-propoxy-1- [1,2,4] triazol-1-ylethylidene) amine (JP-A 79/119 462);
Cyazofamid, 4-chloro-2-cyano-N, N-dimethyl-5- (4-methylphenyl) -1H-imidazole-1-sulfonamide (CAS RN 120116-88-3);
Benomyl, N-butyl-2-acetylaminobenzimidazole-1-carboxamide (US 3 631 176);
Carbendazim, (1H-benzoimidazol-2-yl) -methyl carbamate (US 3 657 443);
Thiabendazole, 2- (1,3-thiazol-4-yl) benzimidazole (US 3 017 415);
Fuberidazole, 2- (2-furanyl) -1H-benzimidazole (DE 12 09 799);
Ethaboxam, N- (cyano-2-thienylmethyl) -4-ethyl-2- (ethylamino) -5-thiazolecarboxamide (EP-A 639 574);
Etridiazole;
Himexazole, 5-methyl-1,2-oxazol-3-ol (JP 518249, JP 532202);
Azoxystrobin, methyl 2- {2- [6- (2-cyano-1-vinylpenta-1,3-dienyloxy) pyrimidin-4-yloxy] phenyl} -3-methoxyacrylate (EP-A 382 375) ;
Dimoxystrobin, (E) -2- (methoxyimino) -N-methyl-2- [α- (2,5-xylyloxy) -o-tolyl] acetamide (EP-A 477 631);
Fluoxastrobin, (E)-{2- [6- (2-chlorophenoxy) -5-fluoropyrimidin-4-yloxy] phenyl} (5,6-dihydro-1,4,2-dioxazin-3- Yl) methanone O-methyl oxime (WO 97/27189);
Cresoxime-methyl, methyl (E) -methoxyimino [α- (o-tolyloxy) -o-tolyl] acetate (EP-A 253 213);
Metminostrobin, (E) -2- (methoxyimino) -N-methyl-2- (2-phenoxyphenyl) acetamide (EP-A 398 692);
Orisatrobin, (2E) -2- (methoxyimino) -2- {2-[(3E, 5E, 6E) -5- (methoxyimino) -4,6-dimethyl-2,8-dioxa-3,7- Diazanona-3,6-dien-1-yl] phenyl} -N-methylacetamide (WO 97/15552);
Picoxystrobin, methyl 3-methoxy-2- [2- (6-trifluoromethylpyridin-2-yloxymethyl) phenyl] acrylate (EP-A 278 595);
Trifloxystrobin, (E) -methoxyimino-{(E) -α- [1- (α, α, α-trifluoro-m-tolyl) ethylideneaminooxy] -o-tolyl} methyl acetate (EP- A 460 575);
Carboxin, 5,6-dihydro-2-methyl-N-phenyl-1,4-oxathiin-3-carboxamide (US 3 249 499);
Benalaxyl, N- (phenylacetyl) -N- (2,6-xylyl) -DL-alanine methyl (DE 29 03 612);
Boscalid, 2-chloro-N- (4′-chlorobiphenyl-2-yl) nicotinamide (EP-A 545 099);
Fenhexamide, N- (2,3-dichloro-4-hydroxyphenyl) -1-methylcyclohexanecarboxamide (Proc. Br. Crop Prot. Conf.- Pests Dis., 1998, Vol. 2, p. 327);
Flutolanil, α, α, α-trifluoro-3'-isopropoxy-o-toluanilide (JP 1104514);
Furametopyr, 5-chloro-N- (1,3-dihydro-1,1,3-trimethyl-4-isobenzofuranyl) -1,3-dimethyl-1H-pyrazole-4-carboxamide [CAS RN 123572-88 -3];
Mepronil, 3'-isopropoxy-o-toluanilide (US 3 937 840);
Metalaxyl, N- (methoxyacetyl) -N- (2,6-xylyl) -DL-alanine methyl (GB 15 00 581);
Mefenoxam, N- (2,6-dimethylphenyl) -N- (methoxyacetyl) -D-alanine methyl;
Off-race, (RS) -α- (2-chloro-N-2,6-xylylacetamido) -γ-butyrolactone [CAS RN 58810-48-3];
Oxadixyl, N- (2,6-dimethylphenyl) -2-methoxy-N- (2-oxo-3-oxazolidinyl) acetamide (GB 20 58 059);
Oxycarboxin, 5,6-dihydro-2-methyl-1,4-oxathiin-3-carboxanilide 4,4-dioxide (US 3 399 214);
Penthiopyrad, N- [2- (1,3-dimethylbutyl) -3-thienyl] -1-methyl-3- (trifluoromethyl) -1H-pyrazole-4-carboxamide (JP 10130268);
Tifluzamide, N- [2,6-dibromo-4- (trifluoromethoxy) phenyl] -2-methyl-4- (trifluoromethyl) -5-thiazolecarboxamide;
Thiazinyl, 3'-chloro-4,4'-dimethyl-1,2,3-thiadiazole-5-carboxanilide [CAS RN 223580-51-6];
Dimethomorph, 3- (4-chlorophenyl) -3- (3,4-dimethoxyphenyl) -1-morpholin-4-ylpropenone (EP-A 120 321);
Fullmorph, 3- (4-fluorophenyl) -3- (3,4-dimethoxyphenyl) -1-morpholin-4-ylpropenone (EP-A 860 438);
Flumetober, 2- (3,4-dimethoxyphenyl) -N-ethyl-α, α, α-trifluoro-N-methyl-p-toluamide [AGROW No. 243, 22 (1995)];
Fluopicolide (picobenzamide), 2,6-dichloro-N- (3-chloro-5-trifluoromethylpyridin-2-ylmethyl) benzamide (WO 99/42447);
Zoxamide, (RS) -3,5-dichloro-N- (3-chloro-1-ethyl-1-methyl-2-oxopropyl) -p-toluamide [CAS RN 156052-68-5];
Carpropamide, 2,2-dichloro-N- [1- (4-chlorophenyl) ethyl] -1-ethyl-3-methylcyclopropanecarboxamide [CAS RN 104030-54-8];
Diclocimet, 2-cyano-N-[(1R) -1- (2,4-dichlorophenyl) ethyl] -3,3-dimethylbutanamide;
Mandipropamide, (RS) -2- (4-chlorophenyl) -N- [3-methoxy-4- (prop-2-ynyloxy) phenethyl] -2- (prop-2-ynyloxy) acetamide [CAS RN 374726-62- 2];
Fluazinam, 3-chloro-N- [3-chloro-2,6-dinitro-4- (trifluoromethyl) phenyl] -5- (trifluoromethyl) -2-pyridinamine (The Pesticide Manual, published by The British Crop Protection Council, 10th edition (1995), p. 474);
Pyriphenox, 1- (2,4-dichlorophenyl) -2- (3-pyridinyl) ethanone O-methyl oxime (EP-A 49 854);
Bupyrimeto, 5-butyl-2-ethylamino-6-methylpyrimidin-4-yldimethylsulfamate [CAS RN 41483-43-6];
Cyprodinil, (4-cyclopropyl-6-methylpyrimidin-2-yl) phenylamine (EP-A 310 550);
Phenarimol, (4-chlorophenyl) (2-chlorophenyl) pyrimidin-5-ylmethanol (GB 12 18 623);
Ferrimzone, (Z) -2'-methylacetophenone 4,6-dimethylpyrimidin-2-ylhydrazone [CAS RN 89269-64-7];
Mepanipyrim, (4-methyl-6-prop-1-ynylpyrimidin-2-yl) phenylamine (EP-A 224 339);
Nualimol, α- (2-chlorophenyl) -α- (4-fluorophenyl) -5-pyrimidinemethanol (GB 12 18 623);
Pyrimethanil, 4,6-dimethylpyrimidin-2-ylphenylamine (DD-A 151 404);
Triphorine, N, N- {piperazine-1,4-diylbis [(trichloromethyl) methylene]} diformamide (DE 19 01 421);
Fenpiclonyl, 4- (2,3-dichlorophenyl) -1H-pyrrole-3-carbonitrile (Proc. 1988 Br. Crop Prot. Conf.- Pests Dis., Vol. 1, p. 65);
Fludioxonil, 4- (2,2-difluorobenzo [1,3] dioxol-4-yl) -1H-pyrrole-3-carbonitrile (The Pesticide Manual, published The British Crop Protection Council, 10th edition (1995), p. 482);
Over 85%, including aldimorph, 4-alkyl-2,5 (or 2,6) -dimethylmorpholine, 65-75% 2,6-dimethylmorpholine and 25-35% 2,5-dimethylmorpholine -Dodecyl-2,5 (or 2,6) -dimethylmorpholine, where "alkyl" may also include octyl, decyl, tetradecyl or hexadecyl, the cis / trans ratio is 1: 1;
Dodemorph, 4-cyclododecyl-2,6-dimethylmorpholine (DE 1198125);
Fenpropimorph, (RS) -cis-4- [3- (4-tert-butylphenyl) -2-methylpropyl] -2,6-dimethylmorpholine (DE 27 52 096);
Tridemorph, 2,6-dimethyl-4-tridecylmorpholine (DE 11 64 152);
Fenpropidin, (RS) -1- [3- (4-tert-butylphenyl) -2-methylpropyl] piperidine (DE 27 52 096);
Iprodione, N-isopropyl-3- (3,5-dichlorophenyl) -2,4-dioxoimidazolidine-1-carboxamide (GB 13 12 536);
Procimidone, N- (3,5-dichlorophenyl) -1,2-dimethylcyclopropane-1,2-dicarboximide (US 3 903 090);
Vinclozoline, 3- (3,5-dichlorophenyl) -5-methyl-5-vinyloxazolidine-2,4-dione (DE-OS 22 07 576);
Famoxadone, (RS) -3-anilino-5-methyl-5- (4-phenoxyphenyl) -1,3-oxazolidine-2,4-dione;
Phenamidon, (S) -1-anilino-4-methyl-2-methylthio-4-phenylimidazolin-5-one;
Octirinone;
Probenazole, 3-allyloxy-1,2-benzothiazole 1,1-dioxide;
Amisulbrom, N, N-dimethyl-3- (3-bromo-6-fluoro-2-methylindole-1-sulfonyl)-[1,2,4] triazole-1-sulfonamide (WO 03/053145);
Anilazine, 4,6-dichloro-N- (2-chlorophenyl) -1,3,5-triazine-2-amine (US 2 720 480);
Dichromedin, 6- (3,5-dichlorophenyl) -p-tolyl) pyridazin-3 (2H) -one;
Pyrokylone;
Proquinazide, 6-iodo-2-propoxy-3-propylquinazolin-4 (3H) -one (WO 97/48684);
Tricyclazole, 5-methyl-1,2,4-triazolo [3,4-b] benzothiazole (GB 14 19 121);
Acibenzoral-S-methyl, methyl benzo [1,2,3] thiadiazole-7-carbothioate;
Captohol, N- (1,1,2,2-tetrachloroethylthio) cyclohex-4-ene-1,2-dicarboximide;
Captan, 2-trichloromethylsulfanyl-3a, 4,7,7a-tetrahydroisoindole-1,3-dione (US 2 553 770);
Dazomet, 3,5-dimethyl-1,3,5-thiadiazinane-2-thione;
Holpet, 2-trichloromethylsulfanylisoindole-1,3-dione (US 2 553 770);
Phenoxanyl, N- (1-cyano-1,2-dimethylpropyl) -2- (2,4-dichlorophenoxy) propanamide;
Quinoxyphene, 5,7-dichloro-4- (4-fluorophenoxy) quinoline (US 5 240 940);
Mancozeb, ethylenebis (dithiocarbamic acid) manganese zinc complex (US 3 379 610);
Maneb, ethylenebis (dithiocarbamate) manganese (US 2 504 404);
Metam, methyl dithiocarbamate (US 2 791 605);
Methylam, ethylenebis (dithiocarbamic acid) zinc ammonia complex (US 3 248 400);
Propinebu, propylene bis (dithiocarbamate) zinc polymer (BE 611 960);
Felbum, iron (3+) dimethyldithiocarbamate (US 1 972 961);
Thiram, bis (dimethylthiocarbamoyl) disulfide (DE 642 532);
Ziram, dimethyldithiocarbamate;
Zineb, zinc ethylenebis (dithiocarbamate) (US 2 457 674);
Dietofencarb, isopropyl 3,4-diethoxycarbanilate;
Iprovaricarb, [(1S) -2-methyl-1- (1-p-tolylethylcarbamoyl) propyl] isopropyl carbamate (EP-A 472 996);
Full bench avaricarb (bench avaricarb), {(S) -1-[(1R) -1- (6-fluorobenzothiazol-2-yl) ethylcarbamoyl] -2-methylpropyl} isopropyl carbamate ( JP-A 09/323 984);
Propamocarb, propyl 3- (dimethylamino) propylcarbamate (DE 16 43 040);
Dodin, (2,4-dichlorophenoxy) acetic acid (US 2 867 562);
Iminotazine, bis (8-guanidinooctyl) amine (GB 11 14 155);
Guazatine, a mixture of products resulting from amidation of iminodi (octamethylene) diamine, i.e. iminotadine;
Kasugamycin, 1L-1,3,4 / 2,5,6-1-deoxy-2,3,4,5,6-pentahydroxycyclohexyl 2-amino-2,3,4,6-tetradeoxy-4- (α-iminoglycino) -α-D-arabino-hexopyranoside;
Streptomycin, O-2-deoxy-2-methylamino-α-L-glucopyranosyl- (1 → 2) -O-5-deoxy-3-C-formyl-α-L-lyxofuranosyl- (1 → 4) N ¹ , N ³ -diamidino-D-streptamine;
Polyoxins, 5- (2-amino-5-O-carbamoyl-2-deoxy-L-xylonamide) -1- (5-carboxy-1,2,3,4-tetrahydro-2,4-dioxopyrimidine- 1-yl) -1,5-dideoxy-β-D-alofurauronic acid and its salts;
Validamycin A, Binapacryl, (RS) -2-sec-butyl-4,6-dinitrophenyl 3-methylcrotonate;
Dinocup, a mixture of 2,6-dinitro-4-octylphenyl crotonate and 2,4-dinitro-6-octylphenyl crotonate, where “octyl” is a mixture of 1-methylheptyl, 1-ethylhexyl and 1-propylpentyl (US 2 526 660);
Dinobutone, (RS) -2-sec-butyl-4,6-dinitrophenyl isopropyl carbonate;
Dithianone, 5,10-dioxo-5,10-dihydronaphtho [2,3-b] [1,4] dithiin-2,3-dicarbonitrile (GB 857 383);
Isoprothiolane, indol-3-ylacetic acid;
Fentin acetate, fentin acetate (US 3 499 086);
Edifenphos, O-ethyl S, S-diphenyl phosphorodithioate;
Iprobenphos, S-benzyl O, O-diisopropyl phosphorothioate (Jpn. Pesticide Inf., No. 2, S. 11 (1970));
Fosetyl, fosetyl-aluminum, (aluminum) ethyl phosphonate (FR 22 54 276);
Pyrazophos, ethyl 2-diethoxyphosphinothioyloxy-5-methylpyrazolo [1,5-a] pyrimidine-6-carboxylate (DE 15 45 790);
Tolcrophos-methyl, O-2,6-dichloro-p-tolyl O, O-dimethyl phosphorothioate (GB 14 67 561);
Chlorothalonil, 2,4,5,6-tetrachloroisophthalonitrile (US 3 290 353);
Dichlorofluanide, N-dichlorofluoromethylthio-N, N-dimethyl-N-phenylsulfamide (DE 11 93 498);
Fursulfamide, 2 ', 4-dichloro-α, α, α-trifluoro-4'-nitro-m-toluenesulfanilide (EP-A 199 433);
Hexachlorobenzene (CR Seances Acad. Agric. Fr., Vol. 31, p. 24 (1945));
Phthalide (DE 16 43 347);
Pencyclon, 1- (4-chlorobenzyl) -1-cyclopentyl-3-phenylurea (DE 27 32 257);
Kintozen, pentachloronitrobenzene (DE 682 048);
Thiophanate-methyl, 1,2-phenylenebis (iminocarbonothioyl) bis (dimethylcarbamate) (DE-OS 19 30 540);
Tolylfuranide, N-dichlorofluoromethylthio-N, N-dimethyl-Np-tolylsulfamide (DE 11 93 498);
Bordeaux liquid, a mixture of calcium hydroxide and copper (II) sulfate;
Copper hydroxide, Cu (OH) ₂ ;
Copper oxychloride, Cu ₂ Cl (OH) ₃ ;
Cyflufenamide, (Z) -N- [α- (cyclopropylmethoxyimino) -2,3-difluoro-6- (trifluoromethyl) benzyl] -2-phenylacetamide (WO 96/19442);
Simoxanyl, 1- (2-cyano-2-methoxyiminoacetyl) -3-ethylurea (US 3 957 847);
Dimethylylmol, 5-butyl-2-dimethylamino-6-methylpyrimidin-4-ol (GB 11 82 584);
Ethymol, 5-butyl-2-ethylamino-6-methylpyrimidin-4-ol (GB 11 82 584);
Flaxyl, N- (2-furoyl) -N- (2,6-xylyl) -DL-alanine methyl (GB 14 48 810);
Metraphenone, 3'-bromo-2,3,4,6'-tetramethoxy-2 ', 6-dimethylbenzophenone (US 5 945 567);
Spiroxamine, (8-tert-butyl-1,4-dioxaspiro [4.5] dec-2-yl) diethylamine (EP-A 281 842).

The compounds named according to IUPAC, their preparation and their bactericidal activity are likewise known:
(2-Chloro-5- [1- (3-methylbenzyloxyimino) ethyl] benzyl) carbamate methyl, (2-chloro-5- [1- (6-methylpyridin-2-ylmethoxyimino) ethyl] Benzyl) methyl carbamate (EP-A 12 01 648);
Methyl 2- (ortho-((2,5-dimethylphenyloxymethylene) phenyl) -3-methoxyacrylate (EP-A 226 917);
5-chloro-7- (4-methylpiperidin-1-yl) -6- (2,4,6-trifluorophenyl)-[1,2,4] triazolo [1,5-a] pyrimidine (WO 98 / 46608);
3,4-dichloro-N- (2-cyanophenyl) isothiazole-5-carboxamide (WO 99/24413);
N- (2- {4- [3- (4-chlorophenyl) prop-2-ynyloxy] -3-methoxyphenyl} ethyl) -2-methanesulfonylamino-3-methylbutyramide, N- (2- {4 -[3- (4-chlorophenyl) prop-2-ynyloxy] -3-methoxyphenyl} ethyl) -2-ethanesulfonylamino-3-methylbutyramide (WO 04/049804);
N- (4'-bromobiphenyl-2-yl) -4-difluoromethyl-2-methylthiazole-5-carboxamide, N- (4'-trifluoromethylbiphenyl-2-yl) -4-difluoromethyl-2 -Methylthiazole-5-carboxamide, N- (4'-chloro-3'-fluorobiphenyl-2-yl) -4-difluoromethyl-2-methylthiazole-5-carboxamide, N- (3 ', 4'- (Dichloro-4-fluorobiphenyl-2-yl) -3-difluoromethyl-1-methylpyrazole-4-carboxamide (WO 03/066609);
N- (3 ′, 4′-dichloro-5-fluorobiphenyl-2-yl) -3-difluoromethyl-1-methylpyrazole-4-carboxamide (WO 03/053145);
2-Butoxy-6-iodo-3-propylchromen-4-one (WO 03/14103);
3- [5- (4-chlorophenyl) -2,3-dimethylisoxazolidin-3-yl] pyridine (EP-A 10 35 122);
Amisulbrom, N, N-dimethyl-3- (3-bromo-6-fluoro-2-methylindole-1-sulfonyl)-[1,2,4] triazole-1-sulfonamide (WO 03/053145);
Methyl 3- (4-chlorophenyl) -3- (2-isopropoxycarbonylamino-3-methylbutyrylamino) propanoate (EP-A 1028125).

  6- (3,4-dichlorophenyl) -5-methyl- [1,2,4] triazolo [1,5-a] pyrimidin-7-ylamine; 6- (4-tert-butylphenyl) -5-methyl- [1,2,4] triazolo [1,5-a] pyrimidin-7-ylamine; 5-methyl-6- (3,5,5-trimethyl-hexyl)-[1,2,4] triazolo [1, 5-a] pyrimidin-7-ylamine; 5-methyl-6-octyl- [1,2,4] triazolo [1,5-a] pyrimidin-7-ylamine; 6-methyl-5-octyl- [1, 2,4] Triazolo [1,5-a] pyrimidin-7-ylamine; 6-ethyl-5-octyl- [1,2,4] triazolo [1,5-a] pyrimidin-7-ylamine; 5-ethyl -6-Octyl- [1,2,4] triazolo [1,5-a] pyrimidin-7-ylamine; 5-ethyl-6- (3,5,5-trimethyl-hexyl)-[1,2,4 ] Triazolo [1,5-a] pyrimidin-7-ylamine; 6-octyl-5-propyl- [1,2,4] triazolo [1,5-a] pyrimidin-7-ylamine; 5-methoxymethyl-6 -Octyl- [1,2,4] triazolo [1,5-a] pyrimidine-7 6-octyl-5-trifluoromethyl- [1,2,4] triazolo [1,5-a] pyrimidin-7-ylamine; and 5-trifluoromethyl-6- (3,5,5- Trimethyl-hexyl)-[1,2,4] triazolo [1,5-a] pyrimidin-7-ylamine can be obtained from EP-A 71 792, EP-A 141 317, WO 03/009687, WO 05/087771, WO Known from 05/087772 (= PCT / EP / 05/002426), WO 05/087773, PCT / EP2006 / 050922 (= WO 2006/087325), and / or PCT / EP2006 / 060399 (= WO 2006/092428) is there.

  N- (2 ', 4'-Difluorobiphenyl-2-yl) -1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxamide; N- (2', 4'-dichlorobiphenyl-2-yl ) -1-Methyl-3-trifluoromethyl-1H-pyrazole-4-carboxamide; N- (2 ', 4'-difluorobiphenyl-2-yl) -3-difluoromethyl-1-methyl-1H-pyrazole- 4-carboxamide; N- (2 ', 4'-dichlorobiphenyl-2-yl) -3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide; N- (2', 5'-difluorobiphenyl- 2-yl) -1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxamide; N- (2 ', 5'-dichlorobiphenyl-2-yl) -1-methyl-3-trifluoromethyl- 1H-pyrazole-4-carboxamide; N- (2 ', 5'-difluorobiphenyl-2-yl) -3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide; N- (2', 5 ' -Dichlorobiphenyl-2-yl) -3-difluoro Tyl-1-methyl-1H-pyrazole-4-carboxamide; N- (3 ', 5'-difluorobiphenyl-2-yl) -1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxamide; N -(3 ', 5'-dichlorobiphenyl-2-yl) -1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxamide; N- (3', 5'-difluorobiphenyl-2-yl) -3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide; N- (3 ', 5'-dichlorobiphenyl-2-yl) -3-difluoromethyl-1-methyl-1H-pyrazole-4- Carboxamide; N- (3'-fluorobiphenyl-2-yl) -1-methyl-3-trifluoromethyl-1H-pyrazol-4-carboxamide; N- (3'-chlorobiphenyl-2-yl) -1- Methyl-3-trifluoromethyl-1H-pyrazole-4-carboxamide; N- (3′-fluorobiphenyl-2-yl) -3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide; N- ( 3'-chlorobi Enyl-2-yl) -3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide; N- (2'-fluorobiphenyl-2-yl) -1-methyl-3-trifluoromethyl-1H- Pyrazole-4-carboxamide; N- (2'-chlorobiphenyl-2-yl) -1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxamide; N- (2'-fluorobiphenyl-2-yl ) -3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide; N- (2′-chlorobiphenyl-2-yl) -3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide; N- (2'-fluoro-4'-chloro-5'-methylbiphenyl-2-yl) -1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxamide; N- (3 ', 4' , 5'-trifluorobiphenyl-2-yl) -1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxamide; N- (3 ', 4', 5'-trifluorobiphenyl-2-yl ) -1-Methyl-3-difluorome 1H-pyrazole-4-carboxamide; N- (2 ', 4', 5'-trifluorobiphenyl-2-yl) -1-methyl-3-difluoromethyl-1H-pyrazole-4-carboxamide; N- (3 ', 4', 5'-trifluorobiphenyl-2-yl) -3-chlorofluoromethyl-1-methyl-1H-pyrazole-4-carboxamide; N- [2- (1,1,2,3 , 3,3-Hexafluoropropoxy) phenyl] -1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxamide; N- [2- (1,1,2,3,3,3-hexafluoro Propoxy) -phenyl] -3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide; N- [2- (2-chloro-1,1,2-trifluoroethoxy) phenyl] -1-methyl- 3-trifluoromethyl-1H-pyrazole-4-carboxamide; N- [2- (2-chloro-1,1,2-trifluoroethoxy) phenyl] -3-difluoromethyl-1-methyl-1H-pyrazole- 4-carboxamide; N- [2- (1,1,2,2-tetrafluoroethoxy) Nyl] -3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide; N- [2- (1,1,2,2-tetrafluoroethoxy) phenyl] -1-methyl-3-trifluoromethyl -1H-pyrazole-4-carboxamide; N- (4 '-(trifluoromethylthio) biphenyl-2-yl) -3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide; and N- (4' -(Trifluoromethylthio) biphenyl-2-yl) -1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxamide can be obtained from WO 2006/087343, WO 2001/42223, WO 2005/34628, WO 2005 / 123689, WO 2005/123690, WO 2006/120219, PCT / EP2006 / 064991 (= WO 2007/017450), and / or WO 2008/053044 (early EP application 06123463.9).

In the mixtures according to the invention, at least one compound I and at least one compound II are present in a synergistic amount. This means that the relative amount (ie weight ratio) of at least one compound I and at least one compound II in the mixture is the additive bactericidal effect of the compounds in the mixture (for each compound at a given application rate). It means that the enhancement of the bactericidal effect exceeds that calculated from the bactericidal effect. The calculation of additive bactericidal effects can be calculated, for example, by the Colby equation (Colby, SR “Calculating synergistic and antagonistic responses of herbicide Combinations”), Weeds, 15 20-22, 1967). A synergistic effect exists if the observed effect exceeds the calculated effect.

  In order to ensure a synergistic effect, the at least one compound of formula I and the at least one compound II are usually 500: 1 to 1: 100, preferably 100: 1 to 1: 100, more preferably 50: It is present in the mixture according to the invention in a weight ratio of 1-1: 50, in particular 20: 1 to 1:20.

  According to the invention, binary and ternary mixtures are preferred. A binary mixture is a mixture comprising at least one active compound of formula I (in particular, exactly one compound of formula I) and one fungicidal compound belonging to group II.

  The ternary mixture comprises at least one active compound of formula I (especially exactly one compound of formula I) and two different fungicidal compounds belonging to group II of fungicidal compounds (hereinafter also referred to as compounds IIa and IIb) It is a mixture containing.

  In the binary mixture of the present invention, at least one compound of the formula I and one compound II are usually 500: 1 to 1: 100, preferably 100: 1 to 1: 100, more preferably 50: 1 to It is present in a weight ratio of 1:50, especially 20: 1 to 1:20.

  In the ternary mixture of the present invention, at least one compound of formula I and two compounds IIa and IIb are usually 500: 1 to 1: 100, preferably 100: 1 to 1: 100, more preferably 50: Present in a weight ratio of compound I to compound IIa + IIb from 1 to 1:50, in particular from 20: 1 to 1:20. The weight ratio of the first compound IIa to the second compound IIb is usually in the range of 100: 1 to 1: 100, more preferably 50: 1 to 1:50, especially 20: 1 to 1:20.

  Preferred mixtures are compounds I and the azole series: cyproconazole, difenoconazole, epoxiconazole, fenbuconazole, fluquinconazole, flutriahole, hexaconazole, ipconazole, metconazole, propiconazole, prothioconazole, tebuconazole. And bactericidal compound II selected from the list comprising tetraconazole, triadimenol, triadimethonol, triticonazole, cyazofamide, imazalyl, prochloraz, triflumizole, benomyl, carbendazim, thiabendazole, ethaboxam and hymexazole The original mixture. Particularly preferred are binary mixtures containing compound I and the azole series: bactericidal compound II selected from the list comprising epoxiconazole and cyazofamide.

  Preferred mixtures are selected from the list comprising Compound I and the strobilurin series: azoxystrobin, dimoxystrobin, fluoxastrobin, cresoxime-methyl, methminostrobin, picoxystrobin and trifloxystrobin It is a binary mixture containing bactericidal compound II. Likewise preferred are binary mixtures containing Compound I and the strobilurin system: bactericidal compound II selected from the list comprising pyraclostrobin. Particularly preferred are binary mixtures containing Compound I and the bactericidal compound II selected from the list comprising the strobilurin system: picoxystrobin, pyraclostrobin and trifloxystrobin.

  Preference is given to compound I and the carboxamide series: boscalid, carboxin, benalaxyl, fenhexamide, flutolanil, furamethpyr, metalaxyl, mefenoxam (metalaxyl-M), offlace, oxadixyl, oxycarboxyl, penthiopyrado, tifluzamide, thiazinyl A binary mixture containing dimethomorph, fluopicolide (picobenzamide), and bactericidal compound II selected from the list comprising diclosimet. Particularly preferred are binary mixtures containing compound I and the carboxamide series: bactericidal compound II selected from the list comprising boscalid.

  Preferred are the compounds I and heterocyclic compounds: pyrimethanil, fenpicuronyl, fludioxonil, aldimorph, dodemorph, fenpropimorph, tridemorph, iprodione, prosimidone, famoxadone, phenamidon, octyrinone, probenazole, diclomedin, pyroxilazole, proquinazol, tricylazol , Captan, dazomet, phenoxanyl, and a bactericidal compound II selected from the list comprising quinoxyphene. Particularly preferred are binary mixtures containing compound I and a heterocyclic compound: bactericidal compound II selected from the list comprising pyrimethanil and captan.

  Preference is given to compounds I and the carbamate series: mancozeb, maneb, metam, methylam, felbam, propineb, thiram, dineb, ziram, thiophanate-methyl, dietofencarb, iprovaricarb, propamocarb, and 3- (4-chlorophenyl) -3- A binary mixture containing bactericidal compound II selected from the list comprising methyl (2-isopropoxycarbonylamino-3-methylbutyrylamino) propanoate. Also preferred are binary mixtures containing Compound I and a bactericidal compound II selected from the list comprising full bench avaricarb (bench avaricarb). Particularly preferred are binary mixtures containing Compound I and a fungicidal compound II selected from the list including the carbamate systems: iprovaricarb, propineb and fullbenchavaricarb (benchavaricarb).

Preferred are Compound I and guazatine, streptomycin, validamycin A, vinapacryl, dinocup, dinobutone, dithianon, isoprothiolane, fentin salt (eg, fentin acetate), edifenephos, iprobenphos, fosetyl, pyrazophos, chlorothalonil, diclofluronide, Bactericidal compounds selected from the list including fursulfamide, phthalide, quintozene, tolylfluanid, copper acetate, copper hydroxide, copper oxychloride, basic copper sulfate, sulfur, cyflufenamide, simoxanyl, dimethylylmol, ethylylmol, furaxyl, metolaphenone and spiroxamine A binary mixture containing II. Particularly preferred are binary mixtures containing Compound I and bactericidal compound II selected from the list comprising chlorothalonil.

  A particular embodiment of the invention is a mixture B-1.1 to B-243.1, wherein the compound of formula I is compound I.1 of Table A and compound II is a compound shown in one row of Table B It is.

  A particular embodiment of the invention is a mixture B-1.2 to B-243.2, wherein the compound of formula I is compound I.2 of Table A and compound II is a compound shown in one row of Table B It is.

  A particular embodiment of the invention is a mixture B-1.3 to B-243.3, wherein the compound of formula I is compound I.3 of Table A and compound II is a compound shown in one row of Table B It is.

  A particular embodiment of the invention is a mixture B-1.4 to B-243.4, wherein the compound of formula I is compound I.4 of Table A and compound II is a compound shown in one row of Table B It is.

  A particular embodiment of the invention is a mixture B-1.5 to B-243.5, wherein the compound of formula I is compound I.5 of Table A and compound II is a compound shown in one row of Table B It is.

  A particular embodiment of the invention is a mixture B-1.6 to B-243.6, wherein the compound of formula I is compound I.6 of Table A and compound II is a compound shown in one row of Table B It is.

  A particular embodiment of the invention is a mixture B-1.7 to B-243.7, wherein the compound of formula I is compound I.7 of Table A and compound II is a compound shown in one row of Table B It is.

  A particular embodiment of the invention is a mixture B-1.8 to B-243.8, wherein the compound of formula I is compound I.8 of Table A and compound II is a compound shown in one row of Table B It is.

  A particular embodiment of the invention is a mixture B-1.9 to B-243.9, wherein the compound of formula I is compound I.9 of Table A and compound II is a compound shown in one row of Table B It is.

  A particular embodiment of the invention is a mixture B-1.10 to B-243.10, wherein the compound of formula I is compound I.10 of Table A and compound II is a compound shown in one row of Table B It is.

  A particular embodiment of the invention is a mixture B-1.11 to B-243.11, wherein the compound of formula I is compound I.11 of Table A and compound II is a compound shown in one column of Table B It is.

  A particular embodiment of the invention is a mixture B-1.12 to B-243.12, wherein the compound of formula I is compound I.12 of Table A and compound II is a compound shown in one column of Table B It is.

  A particular embodiment of the invention is a mixture B-1.13 to B-243.13, wherein the compound of formula I is compound I.13 of Table A and compound II is a compound shown in one row of Table B It is.

  A particular embodiment of the invention is a mixture B-1.14 to B-243.14, wherein the compound of formula I is compound I.14 of Table A and compound II is a compound shown in one row of Table B It is.

  A particular embodiment of the invention is a mixture B-1.15 to B-243.15, wherein the compound of formula I is compound I.15 of Table A and compound II is a compound shown in one column of Table B It is.

  A particular embodiment of the invention is a mixture B-1.16 to B-243.16, wherein the compound of formula I is compound I.16 of Table A and compound II is a compound shown in one row of Table B It is.

  A particular embodiment of the invention is a mixture B-1.17 to B-243.17, wherein the compound of formula I is compound I.17 of Table A and compound II is a compound shown in one column of Table B It is.

  A particular embodiment of the invention is a mixture B-1.18 to B-243.18, wherein the compound of formula I is compound I.18 of Table A and compound II is a compound shown in one column of Table B It is.

  A particular embodiment of the invention is the mixture B-1.19 to B-243.19, wherein the compound of formula I is compound I.19 of Table A and compound II is a compound shown in one column of Table B It is.

  A particular embodiment of the invention is a mixture B-1.20 to B-243.20, wherein the compound of formula I is compound I.20 of Table A and compound II is a compound shown in one column of Table B It is.

  A particular embodiment of the invention is a mixture B-1.21 to B-243.21, wherein the compound of formula I is compound I.21 of Table A and compound II is a compound shown in one row of Table B It is.

  A particular embodiment of the invention is a mixture B-1.22 to B-243.22, wherein the compound of formula I is compound I.22 of Table A and compound II is a compound shown in one row of Table B It is.

  A particular embodiment of the invention is a mixture B-1.23 to B-243.23, wherein the compound of formula I is compound I.23 of Table A and compound II is a compound shown in one row of Table B It is.

  A particular embodiment of the invention is a mixture B-1.24 to B-243.24, wherein the compound of formula I is compound I.24 of Table A and compound II is a compound shown in one row of Table B It is.

  A particular embodiment of the invention is a mixture B-1.25 to B-243.25, wherein the compound of formula I is compound I.25 of Table A and compound II is a compound shown in one row of Table B It is.

  A particular embodiment of the invention is the mixture B-1.26 to B-243.26, wherein the compound of formula I is compound I.26 of Table A and compound II is a compound shown in one row of Table B It is.

  A particular embodiment of the invention is a mixture B-1.27 to B-243.27, wherein the compound of formula I is compound I.27 of Table A and compound II is a compound shown in one row of Table B It is.

  A particular embodiment of the invention is a mixture B-1.28 to B-243.28, wherein the compound of formula I is compound I.28 of Table A and compound II is a compound shown in one column of Table B It is.

  A particular embodiment of the invention is a mixture B-1.29 to B-243.29, wherein the compound of formula I is compound I.29 of Table A and compound II is a compound shown in one column of Table B It is.

  A particular embodiment of the invention is a mixture B-1.30 to B-243.30, wherein the compound of formula I is compound I.30 of Table A and compound II is a compound shown in one row of Table B It is.

  A particular embodiment of the invention is a mixture B-1.31 to B-243.31, wherein the compound of formula I is compound I.31 of Table A and compound II is a compound shown in one row of Table B It is.

  A particular embodiment of the invention is a mixture B-1.32 to B-243.32, wherein the compound of formula I is compound I.32 of Table A and compound II is a compound shown in one column of Table B It is.

  A particular embodiment of the invention is a mixture B-1.33 to B-243.33, wherein the compound of formula I is compound I.33 of Table A and compound II is a compound shown in one column of Table B It is.

  A particular embodiment of the invention is a mixture B-1.34 to B-243.34, wherein the compound of formula I is compound I.34 of Table A and compound II is a compound shown in one column of Table B It is.

  A particular embodiment of the invention is a mixture B-1.35 to B-243.35, wherein the compound of formula I is compound I.35 of Table A and compound II is a compound shown in one column of Table B It is.

  A particular embodiment of the invention is a mixture B-1.36 to B-243.36, wherein the compound of formula I is compound I.36 of Table A and compound II is a compound shown in one column of Table B It is.

  A particular embodiment of the invention is a mixture B-1.37 to B-243.37, wherein the compound of formula I is compound I.37 of Table A and compound II is a compound shown in one column of Table B It is.

  A particular embodiment of the invention is a mixture B-1.38 to B-243.38, wherein the compound of formula I is compound I.38 of Table A and compound II is a compound shown in one column of Table B It is.

  A particular embodiment of the invention is a mixture B-1.39 to B-243.39, wherein the compound of formula I is compound I.39 of Table A and compound II is a compound shown in one column of Table B It is.

  A particular embodiment of the invention is a mixture B-1.40 to B-243.40, wherein the compound of formula I is compound I.40 of Table A and compound II is a compound shown in one row of Table B It is.

  A particular embodiment of the invention is a mixture B-1.41 to B-243.41, wherein the compound of formula I is compound I.41 of Table A and compound II is a compound shown in one row of Table B It is.

  A particular embodiment of the invention is a mixture B-1.42 to B-243.42, wherein the compound of formula I is compound I.42 of Table A and compound II is a compound shown in one row of Table B It is.

  A particular embodiment of the invention is a mixture B-1.43 to B-243.43, wherein the compound of formula I is compound I.43 of Table A and compound II is a compound shown in one column of Table B It is.

  A particular embodiment of the invention is a mixture B-1.44 to B-243.44, wherein the compound of formula I is compound I.44 of Table A and compound II is a compound shown in one row of Table B It is.

  A particular embodiment of the invention is a mixture B-1.45 to B-243.45, wherein the compound of formula I is compound I.45 of Table A and compound II is a compound shown in one row of Table B It is.

  A particular embodiment of the invention is a mixture B-1.46 to B-243.46, wherein the compound of formula I is compound I.46 of Table A and compound II is a compound shown in one row of Table B It is.

  A particular embodiment of the invention is a mixture B-1.47 to B-243.47, wherein the compound of formula I is compound I.47 of Table A and compound II is a compound shown in one row of Table B It is.

  A particular embodiment of the invention is a mixture B-1.48 to B-243.48, wherein the compound of formula I is compound I.48 of Table A and compound II is a compound shown in one row of Table B It is.

  A particular embodiment of the invention is a mixture B-1.49 to B-243.49, wherein the compound of formula I is compound I.49 of Table A and compound II is a compound shown in one row of Table B It is.

  A particular embodiment of the invention is a mixture B-1.50 to B-243.50, wherein the compound of formula I is compound I.50 of Table A and compound II is a compound shown in one row of Table B It is.

  A particular embodiment of the invention is a mixture B-1.51 to B-243.51, where the compound of formula I is compound I.51 of Table A and compound II is a compound shown in one row of Table B It is.

  A particular embodiment of the invention is the mixture B-1.52 to B-243.52, wherein the compound of formula I is compound I.52 of Table A and compound II is a compound shown in one column of Table B It is.

  A particular embodiment of the invention is a mixture B-1.53 to B-243.53, wherein the compound of formula I is compound I.53 of Table A and compound II is a compound shown in one row of Table B It is.

  A particular embodiment of the invention is a mixture B-1.54 to B-243.54, wherein the compound of formula I is compound I.54 of Table A and compound II is a compound shown in one row of Table B It is.

  A particular embodiment of the invention is a mixture B-1.55 to B-243.55, wherein the compound of formula I is compound I.55 of Table A and compound II is a compound shown in one row of Table B It is.

  A particular embodiment of the invention is a mixture B-1.56 to B-243.56, wherein the compound of formula I is compound I.56 of Table A and compound II is a compound shown in one column of Table B It is.

  A particular embodiment of the invention is a mixture B-1.57 to B-243.57, wherein the compound of formula I is compound I.57 of Table A and compound II is a compound shown in one row of Table B It is.

  A particular embodiment of the invention is a mixture B-1.58 to B-243.58, wherein the compound of formula I is compound I.58 of Table A and compound II is a compound shown in one column of Table B It is.

  A particular embodiment of the invention is a mixture B-1.59 to B-243.59, wherein the compound of formula I is compound I.59 of Table A and compound II is a compound shown in one row of Table B It is.

  A particular embodiment of the invention is a mixture B-1.60 to B-243.60, wherein the compound of formula I is compound I.60 of Table A and compound II is a compound shown in one column of Table B It is.

  A particular embodiment of the invention is a mixture B-1.61 to B-243.61, wherein the compound of formula I is compound I.61 of Table A and compound II is a compound shown in one column of Table B It is.

  A particular embodiment of the invention is a mixture B-1.62 to B-243.62, wherein the compound of formula I is compound I.62 of Table A and compound II is a compound shown in one row of Table B It is.

  A particular embodiment of the invention is a mixture B-1.63 to B-243.63, wherein the compound of formula I is compound I.63 of Table A and compound II is a compound shown in one column of Table B It is.

  A particular embodiment of the invention is a mixture B-1.64 to B-243.64, wherein the compound of formula I is compound I.64 of Table A and compound II is a compound shown in one row of Table B It is.

  A particular embodiment of the invention is a mixture B-1.65 to B-243.65, wherein the compound of formula I is compound I.65 of Table A and compound II is a compound shown in one row of Table B It is.

  A particular embodiment of the invention is a mixture B-1.66 to B-243.66, wherein the compound of formula I is compound I.66 of Table A and compound II is a compound shown in one row of Table B It is.

  A particular embodiment of the invention is a mixture B-1.67 to B-243.67, wherein the compound of formula I is compound I.67 of Table A and compound II is a compound shown in one column of Table B It is.

  A particular embodiment of the invention is a mixture B-1.68 to B-243.68, wherein the compound of formula I is compound I.68 of Table A and compound II is a compound shown in one row of Table B It is.

  A particular embodiment of the invention is a mixture B-1.69 to B-243.69, wherein the compound of formula I is compound I.69 of Table A and compound II is a compound shown in one row of Table B It is.

  A particular embodiment of the invention is a mixture B-1.70 to B-243.70, wherein the compound of formula I is compound I.70 of Table A and compound II is a compound shown in one column of Table B It is.

  A particular embodiment of the invention is a mixture B-1.71 to B-243.71, wherein the compound of formula I is compound I.71 of Table A and compound II is a compound shown in one row of Table B It is.

  A particular embodiment of the invention is a mixture B-1.72 to B-243.72, wherein the compound of formula I is compound I.72 of Table A and compound II is a compound shown in one row of Table B It is.

  A particular embodiment of the invention is a mixture B-1.73 to B-243.73, wherein the compound of formula I is compound I.73 of Table A and compound II is a compound shown in one row of Table B It is.

  Particularly preferred are mixtures B-1.1 to B-243.1.

  Particularly preferred are also mixtures B-1.3 to B-243.3.

  For use according to the invention, the mixtures according to the invention, ie compound I and active compound II, can be formulated into conventional preparations such as solutions, emulsions, suspensions, powders, powders, pastes and granules. it can. The use form depends on the particular purpose intended. In any case, it should be ensured that a fine and homogeneous dispersion of the compound according to the invention is achieved.

  The formulations are prepared in a known manner, for example by preparing the active compound with a solvent and / or carrier and optionally adding emulsifiers and dispersants. Examples of the liquid carrier include aqueous and non-aqueous solvents, for example, the following solvents.

Suitable solvents / adjuncts are essentially the following:
-Water, aromatic solvents (eg Solvesso products, xylene), paraffins (eg mineral oil fraction), alcohols (eg methanol, butanol, pentanol, benzyl alcohol), ketones (eg cyclohexanone, γ- Butyrolactone), pyrrolidones (NMP, NOP), acetate esters (glycol diacetate), glycols, fatty acid dimethylamides, fatty acids and fatty acid esters. In principle, mixed solvents can also be used;
-Solid carriers such as ground natural minerals (eg kaolin, clay, talc, chalk) and ground synthetic minerals (eg highly dispersed silica, silicates);
-Emulsifiers, such as nonionic and anionic emulsifiers (eg polyoxyethylene fatty alcohol ethers, alkyl sulfonates and aryl sulfonates) and dispersants (eg lignin sulfite waste liquor and methylcellulose).

  Suitable surfactants are: lignosulfonic acid, naphthalenesulfonic acid, phenolsulfonic acid, dibutylnaphthalenesulfonic acid, alkylarylsulfonic acid, alkylsulfuric acid, alkylsulfonic acid, fatty alcohol sulfuric acid, fatty acid, and sulfuric acid Alkali metal salts, alkaline earth metal salts and ammonium salts of sulfonated fatty alcohol glycol ethers, as well as condensates of sulfonated naphthalene and naphthalene derivatives with formaldehyde, condensates of naphthalene or naphthalene sulfonic acid with phenol and formaldehyde, polyoxy Ethylene octyl phenol ether, ethoxylated isooctyl phenol, octyl phenol, nonyl phenol, alkylphenol polyglycol ether, tributyl phenyl poly Glycol ether, tristearyl phenyl polyglycol ether, alkylaryl polyether alcohol, condensate of alcohol and fatty alcohol ethylene oxide, ethoxylated castor oil, polyoxyethylene alkyl ether, ethoxylated polyoxypropylene, lauryl alcohol polyglycol ether acetal, sorbitol Esters, lignin sulfite waste liquor and methylcellulose.

  Suitable for preparing directly sprayable solutions, emulsions, pastes, or oil dispersions are medium to high boiling mineral oil fractions such as kerosene or diesel oil, as well as coal tar oil, and plant or Oils of animal origin, aliphatic, cyclic and aromatic hydrocarbons such as toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalene or derivatives thereof, methanol, ethanol, propanol, butanol, cyclohexanol, cyclohexanone, isophorone, strong polarity Solvents such as dimethyl sulfoxide, N-methylpyrrolidone, and water.

  In addition, cryoprotectants (eg, glycerin, ethylene glycol, propylene glycol) and bactericides can be added to the formulation.

  Suitable antifoaming agents are for example antifoaming agents based on silicon or magnesium stearate.

  The seed treatment formulation may further comprise a binder and optionally a colorant.

  A binder is added to enhance the adhesion of the active substance to the seed after treatment. Suitable binders are block copolymer EO / PO surfactants, but polyvinyl alcohol, polyvinylpyrrolidone, polyacrylate, polymethacrylate, polybutene, polyisobutylene, polystyrene, polyethyleneamine, polyethyleneamide, polyethyleneimine (Lupasol®) And Polymin®), polyethers, polyurethanes, polyvinyl acetate, tylose, and copolymers derived from these polymers.

  Optionally, a colorant can also be added to the formulation. Suitable colorants or dyes for seed treatment formulations are: Rhodamine B, CI Pigment Red 112, CI Solvent Red 1, Pigment Blue 15: 4, Pigment Blue 15: 3, Pigment Blue 15: 2, Pigment Blue 15: 1, Pigment Blue 80, Pigment Yellow 1, Pigment Yellow 13, Pigment Red 112, Pigment Red 48: 2, Pigment Red 48: 1, Pigment Red 57: 1, Pigment Red 53: 1, Pigment Orange 43, Pigment Orange 34, Pigment Orange 5, Pigment Green 36, Pigment Green 7, Pigment White 6, Pigment Brown 25, Basic Violet 10, Basic Violet 49, Acid Red 51, Acid Red 52, Acid Red 14, Acid Blue 9, Acid Yellow 23 , Basic Red 10, Basic Red 108.

  An example of a gelling agent is carrageenan (Satiagel®).

  Powders, broad-spreads and powders can be produced by mixing the active substance with a solid carrier or by grinding at the same time.

  Granules (eg, coated granules, impregnated granules, homogeneous granules) can be prepared by binding the active compound to a solid support. Examples of solid carriers are mineral earths (eg silica gel, silicate, talc, kaolin, attaclay, limestone, lime, chalk, red clay, ocher, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide) , Ground synthetic materials, fertilizers (eg ammonium sulfate, ammonium phosphate, ammonium nitrate, urea), materials of plant origin (eg flour, bark flour, wood flour, nutshell flour), cellulose powder, and other solid carriers .

  In general, the formulations contain 0.01 to 95% by weight of active compound, preferably 0.1 to 90%. The active compounds are used in a purity of 90% to 100%, preferably 95% to 100% (according to NMR spectrum).

  For seed treatment purposes, each preparation should be diluted 2 to 10 times to obtain an active compound concentration in the ready-to-use preparation of 0.01 to 60% by weight (preferably 0.1 to 40% by weight). it can.

The following are examples of formulations:
1. Products that are diluted with water (if seed treatment is intended, apply the product to the seed after or without dilution)
A) Water-soluble concentrate (SL, LS)
10 parts by weight of the active compound are dissolved in 90 parts by weight of water or a water-soluble solvent. Alternatively, wetting agents or other auxiliaries are added. The active compound dissolves when diluted with water. In this way, a formulation having an active compound content of 10% by weight is obtained.

B) Dispersible concentrated liquid (DC)
20 parts by weight of the active compound are dissolved in 70 parts by weight of cyclohexanone with addition of 10 parts by weight of a dispersant (eg polyvinylpyrrolidone). Dilution with water gives a dispersant. The active compound content is 20% by weight.

C) Emulsifiable concentrate (EC)
15 parts by weight of the active compound are dissolved in 75 parts by weight of xylene with addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (5 parts each). Dilution with water gives an emulsion. The active compound content of the formulation is 15% by weight.

D) Emulsion (EW, EO, ES)
25 parts by weight of the active compound are dissolved in 35 parts by weight of xylene with the addition of calcium dodecylbenzenesulfonate and ethoxylated castor oil (5 parts each). This mixture is added to 30 parts by weight of water using an emulsifier (eg Ultraturrax) to make a homogeneous emulsion. Dilution with water gives an emulsion. The active compound content of the formulation is 25% by weight.

E) Suspension (SC, OD, FS)
In a stirred ball mill, 20 parts by weight of the active compound are ground by adding 10 parts by weight of a dispersant and a wetting agent and 70 parts by weight of water or an organic solvent to obtain a fine active compound suspension. Dilution with water gives a stable suspension of the active compound. The active compound content of the formulation is 20% by weight.

F) Water-dispersible granules and water-soluble granules (WG, SG)
50 parts by weight of the active compound are finely ground with addition of 50 parts by weight of a dispersant and a wetting agent, and water-dispersible or water-soluble Prepare granules. Dilution with water gives a stable dispersion or solution of the active compound. The active compound content of the formulation is 50% by weight.

G) Water-dispersible powder and water-soluble powder (WP, SP, SS, WS)
75 parts by weight of active compound are ground in a rotor stator mill with the addition of 25 parts by weight of dispersant and wetting agent and silica gel. Dilution with water gives a stable dispersion or solution of the active compound. The active compound content of the formulation is 75% by weight.

H) Gel (GF)
In a ball mill, a fine suspension is obtained by grinding 20 parts by weight of active compound, 10 parts by weight of dispersant, 1 part by weight of gelling agent and 70 parts by weight of water or organic solvent. Dilution with water gives a stable suspension, the active compound content of which is 20% by weight.

2. Products applied without dilution
I) dusting agent (DP, DS)
5 parts by weight of active compound are finely ground and mixed thoroughly with 95 parts by weight of finely divided kaolin. This gives a dusting product having an active compound content of 5% by weight.

J) Granules (GR, FG, GG, MG)
0.5 parts by weight of active compound are ground finely and combined with 99.5 parts by weight of support. Current methods are extrusion, spray drying or fluidized bed. This gives granules to be applied undiluted, the active compound content of which is 0.5% by weight.

K) ULV liquid (UL)
10 parts by weight of the active compound are dissolved in 90 parts by weight of an organic solvent (eg xylene). This gives a product to be applied undiluted, the active compound content of which is 10% by weight.

  For seed treatment, usually water-soluble concentrate (LS), suspension (FS), dusting powder (DS), water-dispersible and water-soluble powder (WS, SS), emulsion (ES), emulsifying Concentrated liquid (EC) and gel (GF) are used. These formulations are undiluted, preferably diluted and applied to the seeds. Application to seeds can be done before sowing.

  In a preferred embodiment, the FS agent is used for seed treatment. Generally, FS agent is 1-800 g / L active ingredient, 1-200 g / L surfactant, 0-200 g / L antifreeze, 0-400 g / L binder, 0-200 g / L And up to 1 liter of solvent (preferably water).

  The mixtures according to the invention can be used as such or in the form of their preparations or in the use forms prepared from such preparations, for example directly sprayable solutions, powders, suspensions or dispersions, It can be used in the form of emulsions, oil dispersions, pastes, powders, broad sprays, or granules by spraying, spraying, spraying, broad spraying or watering. The use form depends solely on the intended purpose, but in any case it should be ensured that the active ingredient according to the invention is dispersed as finely as possible.

  Aqueous use forms can be prepared by adding water to a concentrated emulsion, paste or wettable powder (sprayable powder, oil dispersion). For preparing emulsions, pastes or oil dispersions, the active substance is homogenized in water as it is or dissolved in oil or solvent and using a wetting agent, tackifier, dispersant or emulsifier. Alternatively, a concentrate containing the active substance, wetting agent, tackifier, dispersant or emulsifier, and optionally a solvent or oil can be prepared, but such concentrate is suitable for dilution with water. .

  The concentration of the active compound in ready-to-use formulations can vary within a relatively wide range. In general, the concentration is from 0.0001 to 10%, preferably from 0.01 to 1%.

  The active compounds can also be used successfully in the ultra-low-volume (ULV) method, and it is possible to apply formulations containing more than 95% by weight of active compounds It is even possible to apply active ingredients which do not contain.

  Various types of oils, wetting agents, auxiliaries, herbicides, fungicides, other insecticides or bactericides, if appropriate, can be added to the active compound immediately before use (tank mix). These agents can be mixed with the mixtures according to the invention in a weight ratio of 1: 100 to 100: 1, preferably 1:10 to 10: 1.

  The composition of the present invention may also contain fertilizers (eg, ammonium nitrate, urea, potassium carbonate, superphosphate), plant harmful substances, plant growth regulators and safeners. These can be used sequentially or in combination with the above composition, and can also be added immediately before use as appropriate (tank mix). For example, the plant of the present invention may be sprayed before or after applying the fertilizer.

  The compounds may be applied simultaneously (ie, together or separately) or sequentially, but in the case of separate applications, the order generally does not affect the results of the control measures.

Advantageously, they are suitable for controlling the following plant diseases:
Species of the genus Alternaria: occurring in vegetables, rape, sugar beet, fruits, rice, for example A. solani (potato rot fungus, tomato ring rot) or A. alternata (black spot fungus) of potato and tomato ;
・ Species of the genus Aphanomyces: occurring in sugar beets and vegetables;
・ Species of the genus Ascochyta: occurring in cereals and vegetables;
Bipolaris species and Drechslera species: occurring in corn, cereals, rice, turf, such as corn D. maydis (sesame leaf blight);
・ Blumeria graminis: found in cereals;
Botrytis cinerea: found in strawberries, vegetables, flowers and vines;
・ Bremia lactucae: occurring in lettuce;
・ Cercospora species: found in corn, soybean, rice and sugar beet;
・ Species of the genus Cochliobolus: occurring in corn, cereals, rice, for example, Cochliobolus sativus in cereals, Cochliobolus miyabeanus in rice (sesame leaf blight);
-Species of the genus Colletotrichum: occurring in soybeans and cotton;
・ Drechslera species, Pyrenophora species: found in corn, cereals, rice, turf, eg barley D. teres, wheat D. tritici-repentis ;
・ Esca disease (Esca): occurring in vines, causative fungi Phaeocremonium chlamydosporium, Ph. Aleophilum and Formitipora punctata (synonyms Phellinus punctatus);
・ Exserohilum species: found in corn;
・ Erysiphe cichoracearum (powder mold) and Sphaerotheca fuliginea (powder mold): occurring in cucumber;
Fusarium species and Verticillium species: occurring in various plants, such as cereals F. graminearum or F. culmorum, many plants ( Tomato etc.) F. oxysporum (wilt fungus);
・ Gaeumannomyces graminis: occurring in cereals;
・ Gibberella species: occurring in cereals and rice, for example, Gibberella fujikuroi of rice
・ Grainstaining complex: occurring in rice;
・ Helminthosporium species: found in corn and rice;
• Microdochium nivale: found in cereals;
Species of the genus Mycosphaerella: occurring in cereals, bananas, peanuts, eg, wheat M. graminicola (leaf blight fungus), banana M. fijiensis (black sigatoka fungus);
Species of the genus Peronospora: occurring in cabbage, bulbous plants, eg cabbage P. brassicae, onion P. destructor;
・ Phakopsora pachyrhizi (Rust fungus) and Phakopsora meibomiae (Rust fungus): occurring in soybean;
-Species of the genus Phomopsis: occurring in soybeans and sunflowers;
・ Phytophthora infestans: found in potatoes and tomatoes;
・ Species of the genus Phytophthora: occurring in various plants, such as pepper P. capsici (gray plague);
・ Plasmopara viticola: an occurrence in vines;
・ Podosphaera leucotricha: found in apples;
・ Pseudocercosporella herpotrichoides: occurring in cereals;
Pseudoperonospora: found in various plants, such as cucumber P. cubensis, hop P. humili (powdery mildew);
Species of the genus Puccinia: occurring in various plants, for example P. triticina, P. striiformis, P. hordei, or P. graminis of cereals Pathogen), P. asparagi of asparagus (rust fungus);
・ Pyricularia oryzae (rice blast fungus), Corticium sasakii (rice blight fungus), Sarocladium oryzae (leaf rot fungus), S. attenuatum (brown rice fungus), Entyloma oryzae (black rot fungus): occurring in rice;
・ Pyricularia grisea: found in turf and cereals;
-Pythium species: turf, rice, corn, cotton, oilseed rape, sunflower, sugar beet, vegetables, other plants, such as P. ultiumum of various plants, P. aphanidermatum of turf (Withering fungus);
Species of the genus Rhizoctonia: cotton, rice, potato, turf, corn, oilseed rape, potato, sugar beet, vegetables, other plants, eg sugar beet and various plants R. solani (leaf rot fungus);
・ Rhynchosporium secalis: found in barley, rye and triticale;
・ Species of the genus Sclerotinia: occurring in rape and sunflower;
-Septoria tritici (Still blight fungus) and Stagonospora nodorum (Blight fungus): occurring in wheat;
・ Erysiphe (synonym Uncinula) necator: found in vines;
・ Species of the genus Setospaeria: found in corn and turf;
・ Sphacelotheca reiliana (Scab fungus): Occurs in corn;
・ Thievaliopsis species: Occurring in soybean and cotton;
・ Species of the genus Tilletia: occurring in cereals;
-Species of the genus Ustilago: occurring in cereals, corn, sugarcane, eg corn U. maydis (smut fungus);
Venturia species (black scab): Occurs in apples and pears, for example, V. inaequalis of apples (black scab).

  Furthermore, the mixtures according to the invention are suitable for the control of harmful fungi when protecting materials (eg wood, paper, paints, fibers or textiles) and when protecting stored goods. Harmful fungi of particular interest in protecting wood are the following: Ascomycetes, for example, Ophiostoma spp., Ceratocystis spp., Black yeast ( Aureobasidium pullulans), Sclerophoma spp., Ketomium spp., Humicola spp., Petriella spp., Triturus sp. (Trichurus spp.); Basidiomycetes, for example, Coniophora spp., Coriolus spp., Gloeophyllum spp., Lentinus spp. .), Pleurotus spp., Analia species (Poria spp.), Serpra species (Serpula spp.), And Tyromyces spp .; Deuteromycetes For example, Aspergillus spp., Cladosporium Species (Cladosporium spp.), Penicillium species (Penicillium spp.), Trichoderma species (Trichoderma spp.), Alternaria species (Alternaria spp.), Pesilomyces species (Paecilomyces spp.); And Zygomycetes, such as the species of the genus Mucor spp. In addition, harmful fungi of particular interest in protecting the materials are the following yeasts: Candida spp. And Saccharomyces cerevisae.

  They are in particular various cultivated plants such as bananas, cotton, vegetables (eg cucumbers, beans, cucurbits), barley, gramineous plants, oats, coffee, potatoes, corn, fruits, rice, rye, soybeans, It is important to control the myriad fungi that develop on tomatoes, vines, wheat, ornamental plants, sugarcane, or in many seeds.

  “Growth place” means a plant, seed, soil, region, material or environment in which a pest is growing or may grow.

  In the mixtures according to the invention, at least one compound I and at least one compound II are present in a bactericidal effective amount. In general, a “bactericidal effective amount” is a visible effect on the growth of a target organism (eg, necrosis, death, retardation of growth, inhibition, removal, destruction of a target organism, or the generation and activity of a target organism). It means the amount of the mixture of the present invention or a composition containing the mixture required to achieve an effect such as reduction. The bactericidal effective amount may vary for the various mixtures / compositions used in the present invention. The bactericidal effective amount of the mixture / composition will also vary depending on general conditions such as the desired bactericidal effect and duration, weather, target species, habitat, mode of application and the like.

  Compound I and Compound II are usually applied in a weight ratio of 500: 1 to 1: 100, preferably 100: 1 to 1: 100, more preferably 20: 1 to 1:20, especially 10: 1 to 1:10. To do.

  When preparing a mixture, it is preferred to use pure active compounds I and II, to which additional active compounds against pests (eg insects, arachnids, nematodes), herbicidal or growth Regulatory compounds or fertilizers may be added as further active ingredients, if desired.

  The mixtures according to the invention are utilized by treating fungi or plants, seeds, materials or soils to be protected from fungal attack with a bactericidal effective amount of the active compound. The compound may be applied before or after the fungus infects the material, plant or seed.

  In the method of controlling harmful fungi, the application rate of the mixtures according to the invention is 5 g / ha to 2000 g / ha, preferably 50 to 900 g / ha, in particular 50 to 750 g / ha, depending on the type of compound and the desired effect. It is.

  The mixture of the present invention or a composition comprising the mixture is for protecting a plant from attack or invasion by insects, arachnids or nematodes by contacting the plant or the soil or water in which the plant is growing. Can also be used.

  In the context of the present invention, the term plant refers to the whole plant, a part of the plant, or the propagation material of the plant, ie seed or seedling.

  The treatment may be performed on the seed box before planting in the field.

  Plants that can be treated with the mixtures of the invention include all genetically modified plants or transgenic plants (eg resistant to the action of herbicides, fungicides or insecticides for breeding, including genetic engineering techniques). Crops shown), or plants with improved properties compared to existing plants (eg, produced by traditional breeding methods and / or the production of mutants or by recombinant methods).

  Some of the mixtures of the present invention have osmotic effects and thus can be used not only to protect shoots from leaf pests, but also to treat seeds and roots against soil pests. The term seed treatment includes any suitable seed treatment technique known in the art, such as seed dressing, seed coating, seed dusting, seed soaking, and seed pellet formation.

  Compound I and Compound II are usually applied in a weight ratio of 500: 1 to 1: 100, preferably 20: 1 to 1:50, especially 5: 1 to 1:20.

  Depending on the desired effect, the application rates of the mixtures according to the invention are generally from 5 g / ha to 2000 g / ha, preferably from 50 to 1500 g / ha, in particular from 50 to 750 g / ha.

  The mixtures according to the invention are also suitable for protecting seeds and seedlings and shoots, preferably seeds, from soil pests.

Compositions, particularly useful for seed treatment, are for example:
A Soluble concentrate (SL, LS)
D Emulsion (EW, EO, ES)
E Suspension (SC, OD, FS)
F Water-dispersible granules and water-soluble granules (WG, SG)
G Water-dispersible powder and water-soluble powder (WP, SP, WS)
H Gel preparation (GF)
I dusting agent (DP, DS).

  FS agents are preferred.

  In the treatment of seeds, the application rate of the mixtures according to the invention is generally between 0.001 and 10 kg per 100 kg of seeds, depending on the desired effect and seed type. The application rate is preferably 1-1000 g per 100 kg seed, more preferably 1-750 g / 100 kg, in particular 5-500 g / 100 kg. Separate or joint application of Compound I and II, or a mixture of Compound I and II, by spraying or spraying seeds, seedlings, plants, or soil (before or after sowing, or before or after emergence) Do.

  The present invention also comprises a mixture as defined above, or a composition comprising a mixture of two or more active ingredients, or a mixture of two or more compositions, each providing one active ingredient. It relates to propagation material of plants (ie coated and / or containing), in particular seeds. Said seed comprises the mixture according to the invention in an amount of 0.1 g to 10 kg per 100 kg of seed.

  The mixtures according to the invention can be fed both through contact (contact with soil, glass, walls, mosquito nets, carpets, plant parts or animal parts) and ingestion (food or plant parts), as well as trophallaxis and transfer. Effective through (transfer).

  Preferred application methods are application to water masses, soils, fissures and fissures, pastures, compost piles, sewers, water, floors, walls, or spraying to the surroundings and application by bait.

  The mixture of the present invention and the composition containing the same are made of wooden materials (eg, wood, board, sleepers, etc.) and buildings (eg, houses, barns, factories, etc.), as well as construction materials, furniture, leather products, textiles, It can be used to protect vinyl products, electric wires, cables, etc. from fungi.

Usual application rates in protecting the material are, for example, from 0.01 g to 1000 g of active compound per m ^{2 of} treated material, preferably from 0.1 g to 50 g / m ² .

  When used in spray compositions, the content of the active ingredient mixture is 0.001 to 80% by weight, preferably 0.01 to 50% by weight, most preferably 0.01 to 15% by weight.

  When used in the treatment of crops, the application rate of the active ingredient mixture according to the invention can range from 0.1 g to 4000 g / ha, preferably from 25 g to 600 g / ha, more preferably from 50 g to 500 g / ha.

Biological example
Bactericidal action The bactericidal effect of the compound and the mixture could be demonstrated by the following tests:
The active compounds were prepared separately or together as stock solutions containing 0.25% by weight of active compound in acetone or DMSO. To this solution was added 1 wt.

The percent of the infected leaf area determined visually was converted to an effect as a percentage of the untreated control:
The effect (E) is calculated using the Abbot equation as follows:
E = (1−α / β) ・ 100
α corresponds to fungal infection of treated plants expressed in%, and β corresponds to fungal infection of untreated (control) plants expressed in%.

  Effect 0 means that the level of infection of the treated plant matches that of the untreated control plant; effect 100 means that the treated plant was not infected.

The expected effect of a mixture of active compounds is described by the Colby equation (Colby, SR "Calculating synergistic and antagonistic responses of herbicide Combinations"), Weeds, 15 , 20 -22, 1967) and compared with the observed effects.

Colby's formula:
E = x + y−x · y / 100
E is the expected effect expressed as a percentage of the untreated control when a mixture of active compounds A and B is used at concentrations a and b,
x is the effect expressed as a percentage of the untreated control when active compound A is used at concentration a,
y is the effect expressed as a percentage of the untreated control when active compound B is used at concentration b.

Example 1- Bactericidal control of rice sesame leaf blight caused by Cochliobolus miyabeanus (protective)
The leaves of rice seedlings grown in pots were sprayed with an aqueous suspension containing the active compound of the following concentration prepared from the stock solution to the extent that it flowed down. The plant was air dried. The next day, the plants were infected with an aqueous suspension of Cochliobolus miyabeanus spores. Immediately thereafter, the test plant was transferred to a humidification chamber. After 6 days at 22-24 ° C. and a relative humidity close to 100%, the extent of fungal attack on the leaves was assessed visually with the area of the affected leaves as%.

Microtiter test (Use examples 2 to 5)
The active compound was formulated separately as a stock solution with a concentration of 10,000 ppm in dimethyl sulfoxide. The products epoxiconazole, trifloxystrobin, pyraclostrobin, benchavaricarb and boscalid were used as commercial finished formulations and diluted with water to a predetermined concentration of active compound.

Use Example 2- Activity against Plague Phytophthora infestans (Phytin) in Microtiter Test The stock solution was mixed according to the ratio, dispensed into a microtiter plate (MTP), diluted with water to a predetermined concentration. Subsequently, a spore suspension of Phytophthora infestans containing an aqueous nutrient medium based on bean extract was added. The plate was placed in a steam saturated chamber at a temperature of 18 ° C. MTP was measured at 405 nm on the 7th day after inoculation using an absorption photometer.

  The measured parameters are compared to the growth of the active compound-free control sample (100%) and the pathogen-free and active compound-free blank value, expressed as the relative growth of pathogens in the presence of each active compound (%) ) Was evaluated. These percentages were converted to effects. Effect 0 means that the growth level of the pathogen matches that of the untreated control; effect 100 means that the pathogen was not growing. Table 1 shows the results of these tests.

  The compounds of formula I used were compounds I.1 and I.3.

The bactericidal compound II was selected from:
-Azoles: Epoxyconazole;
-Strobilurin series: picoxystrobin, trifloxystrobin;
-Heterocyclic compounds: captan;
-Other active compounds: chlorothalonil.

Use Example 3- Activity against Blast Fungus Pyricularia oryzae (Pyrior) in Microtiter Plate Test The stock solution was mixed according to the ratio, dispensed into a microtiter plate (MTP), diluted with water to a predetermined concentration. Subsequently, a spore suspension of Pyricularia oryzae in an aqueous biomalt solution was added. The plate was placed in a steam saturated chamber at a temperature of 18 ° C. MTP was measured at 405 nm on the 7th day after inoculation using an absorption photometer.

  The measured parameters are compared to the growth of the active compound-free control sample (100%) and the pathogen-free and active compound-free blank value, expressed as the relative growth of pathogens in the presence of each active compound (%) ) Was evaluated. These percentages were converted to effects. Effect 0 means that the growth level of the pathogen matches that of the untreated control; effect 100 means that the pathogen was not growing. These test results are shown in Table 2.

  The compounds of formula I used were compounds I.1 and I.3.

The bactericidal compound II was selected from:
-Strobilurin series: picoxystrobin, fluoxastrobin

Use Case 4- Activity against Gray Mold Disease Caused by Botrytis cinerea (Botrici) in Microtiter Plate Test Mix stock solution in proportions, dispense into microtiter plate (MTP), dilute with water The default concentration was used. Subsequently, a suspension of Botrytis cinerea spores in an aqueous biomalt solution was added. The plate was placed in a steam saturated chamber at a temperature of 18 ° C. MTP was measured at 405 nm on the 7th day after inoculation using an absorption photometer.

  The measured parameters are compared to the growth of the active compound-free control sample (100%) and the pathogen-free and active compound-free blank value, expressed as the relative growth of pathogens in the presence of each active compound (%) ) Was evaluated. These percentages were converted to effects. Effect 0 means that the growth level of the pathogen matches that of the untreated control; effect 100 means that the pathogen was not growing. Table 3 shows the results of these tests.

  The compounds of formula I used were compounds I.1 and I.3.

The bactericidal compound II was selected from:
-Azoles: cyazofamide, epoxiconazole;
-Carboxamide series: Boscalid;
-Heterocyclic compounds: captan;
-Carbamates: Propineb, Bench Avaricarb, Iprovaricarb.

Use Example 5- Activity against wheat leaf blight caused by Septoria tritici (Septtr) The stock solution was mixed according to the ratio, dispensed into a microtiter plate (MTP), diluted with water to a predetermined concentration. Subsequently, a suspension of Septoria tritici spores in an aqueous biomalt solution was added. The plate was placed in a steam saturated chamber at a temperature of 18 ° C. MTP was measured at 405 nm on the 7th day after inoculation using an absorption photometer.

  The measured parameters are compared to the growth of the active compound-free control sample (100%) and the pathogen-free and active compound-free blank value, expressed as the relative growth of pathogens in the presence of each active compound (%) ) Was evaluated. These percentages were converted to effects. Effect 0 means that the growth level of the pathogen matches that of the untreated control; effect 100 means that the pathogen was not growing. Table 4 shows the results of these tests.

  The compounds of formula I used were compounds I.1 and I.3.

The bactericidal compound II was selected from:
-Azoles: Epoxyconazole;
-Strobilurin series: pyraclostrobin;
-Heterocyclic compound: pyrimethanil.

  These test results show that, due to the strong synergistic effect, the activity of the mixtures according to the invention is considerably higher than that predicted using the Colby equation.

Claims (30)

As an active ingredient
1) Bactericidal compounds of formula I:

[Where:
R ¹ is H, C ₁ -C ₆ -alkyl, C ₁ -C ₆ -alkoxy-C ₁ -C ₆ -alkyl, C ₁ -C ₆ -haloalkyl, aryl or heteroaryl, where the last 2 The cyclic part of the groups is unsubstituted or halogen, C ₁ -C ₄ -alkyl, C ₂ -C ₄ -alkynyl, C ₁ -C ₄ -haloalkyl, C ₁ -C ₄ -alkoxy, C ₁ -C ₄ - alkylthio, C ₁ -C ₄ - haloalkoxy, substituted with one, two or three groups selected from cyano and nitro,
A is a covalent bond or C ₁ -C ₄ -alkylene, where C ₁ -C ₄ -alkylene is unsubstituted or C ₁ -C ₄ -alkyl, C ₁ -C ₄ -haloalkyl, C Can have a substituent selected from ₁ -C ₄ -alkoxy and cyano,
Ar is aryl or heteroaryl, wherein the cyclic portion of the aromatic group is unsubstituted or substituted with 1, 2, 3, 4 or 5 groups R ^a , where the groups R ^a are the same But may be different, halogen, C ₁ -C ₄ -alkyl, C ₂ -C ₄ -alkenyl, C ₂ -C ₄ -alkynyl, C ₁ -C ₄ -haloalkyl, C ₁ -C ₄ -alkoxy, C ₁ -C ₄ - alkylthio, C ₁ -C ₄ - haloalkoxy, C ₁ -C ₄ - haloalkylthio, cyano, nitro, aryl, hetaryl, aryloxy, hetaryl, aryloxy -C ₁ -C ₄ - alkyl And hetaryloxy-C ₁ -C ₄ -alkyl, wherein the cyclic part of the last six groups mentioned here is unsubstituted or halogen, C ₁ -C ₄ -alkyl, C _1- C ₄ -haloalkyl, C ₁ -C ₄ -alkoxy, C ₁ -C ₄ -alkylthio, C ₁ -C ₄ -haloalkoxy, cyano and nito Substituted with 1, 2 or 3 groups selected from
Or a salt thereof;
and
2) Bactericidal compound II selected from A) to F) below:
A) Azaconazole, dinicoazole-M (diniconazole-M), oxpoconazol, uniconazole, 1- (4-chloro-phenyl) -2-([1,2,4] triazole -1-yl) -cycloheptanol, imazalil sulfate, bitertanole, bromuconazole, cyproconazole, difenoconazole, diniconazole, enilconazole enilconazole), epoxiconazole, fenbuconazole, flusilazole, fluquinconazole, flutriafol, hexaconazole, imibenconazole, Ipconazole, metconazole, microbutanil, paclobutrazol, Penconazole, propiconazole, prothioconazole, simeconazole, tebuconazole, tetraconazole, uniconazole-P, triadimenol, triadimefon ), Triticonazole, cyazofamid, imazalyl, pefurazoate, prochloraz, triflumizol, benomyl, carbendazim, carbendazim, fuberidazole, (thiabendazole), ethaboxam, etridiazole, hymexazole, and 1- (4-chloro-phenyl) -1- (propyn-2-yloxy) -3- (4- (3,4- Selected from the group consisting of dimethoxy-phenyl) -isoxazol-5-yl) -propan-2-one Azoles;
B) 2- (2- (6- (3-Chloro-2-methyl-phenoxy) -5-fluoro-pyrimidin-4-yloxy) -phenyl) -2-methoxyimino-N-methyl-acetamide, 3-methoxy -2- (2- (N- (4-methoxy-phenyl) -cyclopropane-carboximidoylsulfanylmethyl) -phenyl) -acrylic acid methyl ester, azoxystrobin, dimoxystrobin , Enestroburin, fluoxastrobin, kresoxim-methyl, metinominostrobin, orysastrobin, picoxystrobin, pyraclostrobin ), Trifloxystrobin, methyl (2-chloro-5- [1- (3-methylbenzyloxyimino) ethyl] benzyl) carbamate, (2-chloro-5- [1- (6-methyl Pyridin-2-ylmethoxyi Roh) ethyl] benzyl) carbamate, and 2- (ortho - ((2,5-dimethylphenyl oxymethylene) phenyl) -3-strobilurin selected from the group consisting of methoxy methyl acrylate;
C) Benalaxyl-M, 2-amino-4-methyl-thiazole-5-carboxylic acid anilide, 2-chloro-N- (1,1,3-trimethyl-indan-4-yl) -nicotine Amide, N- (2- (1,3-Dimethylbutyl) -phenyl) -1,3-dimethyl-5-fluoro-1H-pyrazole-4-carboxylic acid amide, N- (4′-chloro-3 ′, 5-Difluoro-biphenyl-2-yl) -3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid amide, N- (4'-chloro-3 ', 5-difluoro-biphenyl-2-yl ) -3-Trifluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid amide, N- (3 ′, 4′-dichloro-5-fluoro-biphenyl-2-yl) -3-trifluoromethyl- 1-methyl-1H-pyrazole-4-carboxylic acid amide, N- (3 ′, 5-difluoro-4′-methyl-biphenyl-2-yl) -3-difluoromethyl-1-methyl-1H-pyrazole-4 -Carboxylic acid amide, N- (3 ', 5-difluoro-4'-methyl-biphenyl-2-yl) -3-tri Fluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid amide, N- (cis-2-bicyclopropyl-2-yl-phenyl) -3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid Amido, N- (trans-2-bicyclopropyl-2-yl-phenyl) -3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid amide, fluopyram, N- (3-ethyl- 3,5,5-trimethyl-cyclohexyl) -3-formylamino-2-hydroxy-benzamide, oxytetracyclin, silthiofam, N- (6-methoxy-pyridin-3-yl) cyclopropanecarboxylic acid Amides, carboxin, benalaxyl, boscalid, fenhexamid, flutolanil, furametpyr, mepronil, metalaxyl, mefenoxam, mefenoxam off Ofurace, oxadixyl, oxycarboxin, penthiopyrad, thifluzamide, tiadinil, N- (4'-bromobiphenyl-2-yl) -4-difluoro Methyl-2-methylthiazole-5-carboxamide, N- (4'-trifluoromethylbiphenyl-2-yl) -4-difluoromethyl-2-methylthiazole-5-carboxamide, N- (4'-chloro-3 '-Fluorobiphenyl-2-yl) -4-difluoromethyl-2-methylthiazole-5-carboxamide, N- (3', 4'-dichloro-4-fluorobiphenyl-2-yl) -3-difluoromethyl- 1-methylpyrazole-4-carboxamide, N- (3 ′, 4′-dichloro-5-fluorobiphenyl-2-yl) -3-difluoromethyl-1-methylpyrazole-4-carboxamide, 3,4-dichloro- N- (2-cyanophenyl) isothiazole-5-carboxamide, N- (2 ', 4'-difluorobi Enyl-2-yl) -1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxamide, N- (2 ', 4'-dichlorobiphenyl-2-yl) -1-methyl-3-trifluoro Methyl-1H-pyrazole-4-carboxamide, N- (2 ′, 4′-difluorobiphenyl-2-yl) -3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide, N- (2 ′, 4'-dichlorobiphenyl-2-yl) -3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide, N- (2 ', 5'-difluorobiphenyl-2-yl) -1-methyl-3 -Trifluoromethyl-1H-pyrazole-4-carboxamide, N- (2 ', 5'-dichlorobiphenyl-2-yl) -1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxamide, N- (2 ', 5'-Difluorobiphenyl-2-yl) -3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide, N- (2', 5'-dichlorobiphenyl-2-yl) -3 -Difluoromethyl-1-methyl-1H -Pyrazole-4-carboxamide, N- (3 ', 5'-difluorobiphenyl-2-yl) -1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxamide, N- (3', 5 ' -Dichlorobiphenyl-2-yl) -1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxamide, N- (3 ', 5'-difluorobiphenyl-2-yl) -3-difluoromethyl-1 -Methyl-1H-pyrazole-4-carboxamide, N- (3 ', 5'-dichlorobiphenyl-2-yl) -3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide, N- (3' -Fluorobiphenyl-2-yl) -1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxamide, N- (3'-chlorobiphenyl-2-yl) -1-methyl-3-trifluoromethyl -1H-pyrazole-4-carboxamide, N- (3'-fluorobiphenyl-2-yl) -3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide, N- (3'-chlorobiphenyl-2 - ) -3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide, N- (2'-fluorobiphenyl-2-yl) -1-methyl-3-trifluoromethyl-1H-pyrazole-4- Carboxamide, N- (2′-chlorobiphenyl-2-yl) -1-methyl-3-trifluoromethyl-1H-pyrazol-4-carboxamide, N- (2′-fluorobiphenyl-2-yl) -3- Difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide, N- (2′-chlorobiphenyl-2-yl) -3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide, N- (2 '-Fluoro-4'-chloro-5'-methylbiphenyl-2-yl) -1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxamide, N- (3', 4 ', 5'- Trifluorobiphenyl-2-yl) -1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxamide, N- (3 ′, 4 ′, 5′-trifluorobiphenyl-2-yl) -1- Methyl-3-difluoromethyl-1H -Pyrazole-4-carboxamide, N- (2 ', 4', 5'-trifluorobiphenyl-2-yl) -1-methyl-3-difluoromethyl-1H-pyrazole-4-carboxamide, N- (3 ' , 4 ', 5'-trifluorobiphenyl-2-yl) -3-chlorofluoromethyl-1-methyl-1H-pyrazole-4-carboxamide, N- [2- (1,1,2,3,3, 3-hexafluoropropoxy) phenyl] -1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxamide, N- [2- (1,1,2,3,3,3-hexafluoropropoxy)- Phenyl] -3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide, N- [2- (2-chloro-1,1,2-trifluoroethoxy) phenyl] -1-methyl-3-tri Fluoromethyl-1H-pyrazole-4-carboxamide, N- [2- (2-chloro-1,1,2-trifluoroethoxy) phenyl] -3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide N- [2- (1,1,2,2-tetrafluoroethoxy) Nyl] -3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide, N- [2- (1,1,2,2-tetrafluoroethoxy) phenyl] -1-methyl-3-trifluoromethyl -1H-pyrazole-4-carboxamide, N- (4 '-(trifluoromethylthio) biphenyl-2-yl) -3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide, N- (4'- (Trifluoromethylthio) biphenyl-2-yl) -1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxamide, dimethomorph, flumorph, flumetover, fluopicolide (fluopicolide) Picobenzamid), zoxamide, carpropamid, diclocymet, mandipropamid, N- (2- {4- [3- (4-chlorophenyl) prop-2-ynyloxy] -3 -Methoxyphenyl} ethyl) -2-methanesulfonyl No-3-methylbutyramide and N- (2- {4- [3- (4-chlorophenyl) -prop-2-ynyloxy] -3-methoxyphenyl} ethyl) -2-ethanesulfonylamino-3-methyl A carboxamide selected from the group consisting of butyramide;
D) 2,3,5,6-tetrachloro-4-methanesulfonyl-pyridine, 3,4,5-trichloropyridine-2,6-di-carbonitrile, N- (1- (5-bromo-3- Chloropyridin-2-yl) -ethyl) -2,4-dichloronicotinamide, N-[(5-bromo-3-chloropyridin-2-yl) -methyl] -2,4-dichloronicotinamide, diflumetrim ( diflumetorim, nitrapyrin, dodemorph acetate, fluoroimid, blasticidin-S (blasticidin-S), chinomethionat, debacarb, difenzoquat, difenzoquat, difenzoquat, difenzoquat, difenzoquat, difenzoquat Fenzoquat-methylsulfate, oxolinic acid, piperalin, fluazinam, pyrifenox, bupirimate, cyprodinil, fenarimol, ferimzone ), Mepanipyrim (mepanip yrim, nuarimol, pyrimethanil, triforine, fenpiclonil, fludioxonil, aldimorph, dodemorph, fenpropimorph, tridemorph, tridemorph Fenpropidin, iprodione, procymidone, vinclozolin, famoxadone, fenamidone, octhilinone, probenazole, amisulbrom (amisbrom) ), Diclomezine, pyroquilon, proquinazid, tricyclazole, 2-butoxy-6-iodo-3-propylchromen-4-one, acibenzolar-S-methyl ), Captafol, captan, dazomet (d azomet), folpet, phenoxanil, quinoxyfen, 3- [5- (4-chlorophenyl) -2,3-dimethylisoxazolidin-3-yl] pyridine, 5-chloro-7- (4-Methylpiperidin-1-yl) -6- (2,4,6-trifluorophenyl)-[1,2,4] triazolo [1,5-a] pyrimidine, 6- (3,4-dichlorophenyl ) -5-Methyl- [1,2,4] triazolo [1,5-a] pyrimidin-7-ylamine, 6- (4-tert-butylphenyl) -5-methyl- [1,2,4] triazolo [1,5-a] pyrimidin-7-ylamine, 5-methyl-6- (3,5,5-trimethylhexyl)-[1,2,4] triazolo [1,5-a] pyrimidin-7-ylamine 5-methyl-6-octyl- [1,2,4] triazolo [1,5-a] pyrimidin-7-ylamine, 6-methyl-5-octyl- [1,2,4] triazolo [1,5 -a] pyrimidin-7-ylamine, 6-ethyl-5-octyl- [1,2,4] triazolo [1,5-a] pyrimidin-7-ylamine, 5-ethyl-6-octyl- [1,2 , 4] bird Azolo [1,5-a] pyrimidin-7-ylamine, 5-ethyl-6- (3,5,5-trimethylhexyl)-[1,2,4] triazolo [1,5-a] pyrimidine-7- Ylamine, 6-octyl-5-propyl- [1,2,4] triazolo [1,5-a] pyrimidin-7-ylamine, 5-methoxymethyl-6-octyl- [1,2,4] triazolo [1 , 5-a] pyrimidin-7-ylamine, 6-octyl-5-trifluoromethyl- [1,2,4] triazolo [1,5-a] pyrimidin-7-ylamine, and 5-trifluoromethyl-6 A heterocyclic compound selected from the group consisting of-(3,5,5-trimethylhexyl)-[1,2,4] triazolo [1,5-a] pyrimidin-7-ylamine;
E) methasulfocarb, propamocarb hydrochlorid, mancozeb, maneb, metam, metyram, ferbam, propineb, thiram ), Zineb, ziram, thiophanate-methyl, dietofencarb, iprovalicarb, flubenthiavalicarb (benthiavalicarb), propamocarb (propamocarb), N- (1- (1- (4-cyanophenyl) ethanesulfonyl) -but-2-yl) carbamate 4-fluorophenyl, and 3- (4-chlorophenyl) -3- (2-iso A carbamate selected from the group consisting of methyl propoxycarbonylamino-3-methylbutyrylamino) propanoate;
And
F) Guanidine: dodine, iminoctadine, guazatine, dodin free base, guazatine-acetate, iminoctadine triacetate;
Antibiotics: kasugamycin, streptomycin, polyoxin, validamycin A;
Nitrophenyl derivatives: binapacryl, dinocap, dinobuton;
Sulfur-containing heterocyclic compounds: dithianon, isoprothiolane;
Organometallic compounds: fentin salts, such as fentin acetate;
Organophosphorus compounds: edifenphos, iprobenfos, fosetyl, fosetyl-aluminum, phosphorous acid and its salts, pyrazophos, tolclofos-methyl;
Organochlorine compounds: chlorothalonil, dichlofluanid, flusulfamide, hexachlorobenzene, phthalide, pencycuron, quintozene, tolylfluanid;
Inorganic active compounds: Bordeaux solution, copper acetate, copper hydroxide, copper oxychloride, basic copper sulfate, sulfur;
Others: cyflufenamid, cymoxanil, dimethirimol, etirimol, flaxaxyl, metrafenone, spiroxamine, iminoctadine-trisalbesylate (iminoctalbesilate) ), Kasugamycin hydrochloride hydrate, dichlorophen, pentachlorophenol and its salts, N- (4-chloro-2-nitro-phenyl) -N-ethyl-4-methyl-benzenesulfonamide, dichloran, nitrotar -Isopropyl, technazen, biphenyl, bronopol, diphenylamine, mildiomycin, oxine-copper, prohexadione calcium, N- (cyclopropylmethoxyimino- (6-difluoro-methoxy-2, 3-Difluoro-phenyl) -methyl) -2-phenylacetamide, N '-(4- (4 -Chloro-3-trifluoromethyl-phenoxy) -2,5-dimethyl-phenyl) -N-ethyl-N-methylformamidine, N '-(4- (4-fluoro-3-trifluoromethyl-phenoxy) -2,5-dimethyl-phenyl) -N-ethyl-N-methylformamidine, N '-(2-methyl-5-trifluoromethyl-4- (3-trimethylsilanyl-propoxy) -phenyl) -N -Ethyl-N-methylformamidine, and N '-(5-difluoromethyl-2-methyl-4- (3-trimethylsilanyl-propoxy) -phenyl) -N-ethyl-N-methylformamidine;
Other active compounds selected from the group consisting of:
A sterilizing mixture comprising a synergistically effective amount. Ar is phenyl and the phenyl is unsubstituted or halogen, C ₁ -C ₄ -alkyl, C ₂ -C ₄ -alkenyl, C ₂ -C ₄ -alkynyl, C ₁ -C ₄ -haloalkyl, _1, 2 or selected from C ₁ -C ₄ -alkoxy, C ₁ -C ₄ -alkylthio, C ₁ -C ₄ -haloalkoxy, C ₁ -C ₄ -haloalkylthio, cyano, nitro, phenoxy and pyridyloxy Substituted with 3 groups, where the last 2 groups listed here are unsubstituted or halogen, C ₁ -C ₄ -alkyl, C ₁ -C ₄ -haloalkyl, C ₁ -C ₄ - alkoxy, C ₁ -C ₄ - haloalkoxy, comprising a compound of formula I which are substituted with 1, 2 or 3 radicals selected from cyano and nitro, mixture of claim 1.   Ar is phenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 2,4-dichlorophenyl, 2,3-dichlorophenyl, 3,4-dichlorophenyl, 2 , 6-dichlorophenyl, 2-chloro-4-fluorophenyl, 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl, 2,4-difluorophenyl, 2,5-difluorophenyl, 3,5-difluorophenyl, 3,4-difluorophenyl, 3-chloro-4-fluorophenyl, 4-chloro-2-fluorophenyl, 2-chloro-5-trifluoromethylphenyl, 2-fluoro-4-trifluoromethylphenyl, 2-fluoro -5-trifluoromethylphenyl, 3-fluoro-5-trifluoromethylphenyl, 2-chloro-3-trifluoromethylphenyl, 4-fluoro-3-trifluoromethylphenyl, 4-methyl B-3-trifluoromethylphenyl, 3-chloro-4-methylphenyl, 2-trifluoromethylphenyl, 3-trifluoromethylphenyl, 4-trifluoromethylphenyl, 3-methoxyphenyl, 4-methoxyphenyl, 3 -Trifluoromethoxyphenyl, 4-trifluoromethoxyphenyl, 4-chloro-3,5-dimethylphenyl, 4-bromo-2,6-dimethylphenyl, 4- (4-chlorophenoxy) phenyl, 4-phenoxyphenyl, 3- (5-chloropyridin-2-yl) oxyphenyl, 3- (5-trifluoromethylpyridin-2-yl) oxyphenyl, 4- (5-chloropyridin-2-yl) oxyphenyl, 4- ( 5-trifluoromethylpyridin-2-yl) oxyphenyl, 3- (2-chloro-6-fluoro-4-trifluoromethylphenoxy) phenyl, 4- (2-chloro-6-fluoro-4-trifluoromethyl) Phenoxy) phenyl, 3- (2,6- Chloro-4-trifluoromethylphenoxy) phenyl, 4- (2,6-dichloro-4-trifluoromethylphenoxy) phenyl, 2,3,4,5-tetrafluorophenyl and pentafluorophenyl The mixture according to claim 1 or 2, comprising the compound of: A comprises a compound of Formula I is a covalent bond or CH _2, a mixture according to any one of claims 1 to 3. R ¹ is H or C ₁ -C ₆ - comprising a compound of Formula I is alkyl, mixture according to any one of claims 1 to 4. R ¹ is phenyl or thienyl, wherein the cyclic part of said group is unsubstituted or halogen, C ₁ -C ₄ -alkyl, C ₂ -C ₄ -alkynyl, C ₁ -C ₄ -haloalkyl, A compound of formula I substituted with 1, 2 or 3 groups selected from C ₁ -C ₄ -alkoxy, C ₁ -C ₄ -alkylthio, C ₁ -C ₄ -haloalkoxy, cyano and nitro 5. A mixture according to any one of claims 1 to 4 comprising. R ¹ is phenyl, 3-chlorophenyl, 4-chlorophenyl, 3-fluorophenyl, 4-fluorophenyl, 4-methoxyphenyl, 3,4-dichlorophenyl, 3,5-dichlorophenyl, 2,5-dichlorophenyl, 3,4- Difluorophenyl, 3,5-difluorophenyl, 2,5-difluorophenyl, benzothien-2-yl, 2-thienyl, 5-chloro-2-thienyl, 3-methyl-2-thienyl, 5-methyl-2-thienyl 7. A mixture according to claim 6, comprising a compound of formula I which is 3-thienyl, 2-methyl-3-thienyl, 2-chloro-3-thienyl or 4-methyl-3-thienyl. R ¹ is hydrogen,
Ar is phenyl and the phenyl is unsubstituted or halogen, C ₁ -C ₄ -alkyl, C ₂ -C ₄ -alkenyl, C ₂ -C ₄ -alkynyl, C ₁ -C ₄ -haloalkyl, _1, 2 or selected from C ₁ -C ₄ -alkoxy, C ₁ -C ₄ -alkylthio, C ₁ -C ₄ -haloalkoxy, C ₁ -C ₄ -haloalkylthio, cyano, nitro, phenoxy and pyridyloxy Substituted with 3 groups, where the last 2 groups listed here are unsubstituted or halogen, C ₁ -C ₄ -alkyl, C ₁ -C ₄ -haloalkyl, C ₁ -C Substituted with 1, 2 or 3 groups selected from ₄ -alkoxy, C ₁ -C ₄ -haloalkoxy, cyano and nitro,
A is a covalent bond or CH ₂ ,
6. A mixture according to any one of claims 1 to 5, comprising a compound of formula I or a salt thereof. R ¹ is hydrogen,
Ar is phenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 2,4-dichlorophenyl, 2,3-dichlorophenyl, 3,4-dichlorophenyl, 2 , 6-dichlorophenyl, 2-chloro-4-fluorophenyl, 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl, 2,4-difluorophenyl, 2,5-difluorophenyl, 3,5-difluorophenyl, 3,4-difluorophenyl, 3-chloro-4-fluorophenyl, 4-chloro-2-fluorophenyl, 2-chloro-5-trifluoromethylphenyl, 2-fluoro-4-trifluoromethylphenyl, 2-fluoro -5-trifluoromethylphenyl, 3-fluoro-5-trifluoromethylphenyl, 2-chloro-3-trifluoromethylphenyl, 4-fluoro-3-trifluoromethylphenyl, 4-methyl B-3-trifluoromethylphenyl, 3-chloro-4-methylphenyl, 2-trifluoromethylphenyl, 3-trifluoromethylphenyl, 4-trifluoromethylphenyl, 3-methoxyphenyl, 4-methoxyphenyl, 3 -Trifluoromethoxyphenyl, 4-trifluoromethoxyphenyl, 4-chloro-3,5-dimethylphenyl, 4-bromo-2,6-dimethylphenyl, 4- (4-chlorophenoxy) phenyl, 4-phenoxyphenyl, 3- (5-chloropyridin-2-yl) oxyphenyl, 3- (5-trifluoromethylpyridin-2-yl) oxyphenyl, 4- (5-chloropyridin-2-yl) oxyphenyl, 4- ( 5-trifluoromethylpyridin-2-yl) oxyphenyl, 3- (2-chloro-6-fluoro-4-trifluoromethylphenoxy) phenyl, 4- (2-chloro-6-fluoro-4-trifluoromethyl) Phenoxy) phenyl, 3- (2,6- Chloro-4-trifluoromethylphenoxy) phenyl, 4- (2,6-dichloro-4-trifluoromethylphenoxy) phenyl, are selected from 2,3,4,5-tetrafluorophenyl and pentafluorophenyl,
A is CH ₂
6. A mixture according to any one of claims 1 to 5, comprising a compound of formula I or a salt thereof. R ¹ is phenyl or thienyl, wherein the cyclic part of said group is unsubstituted or halogen, C ₁ -C ₄ -alkyl, C ₂ -C ₄ -alkynyl, C ₁ -C ₄ -haloalkyl, Substituted with 1, 2 or 3 groups selected from C ₁ -C ₄ -alkoxy, C ₁ -C ₄ -alkylthio, C ₁ -C ₄ -haloalkoxy, cyano and nitro,
Ar is phenyl and the phenyl is unsubstituted or halogen, C ₁ -C ₄ -alkyl, C ₂ -C ₄ -alkenyl, C ₂ -C ₄ -alkynyl, C ₁ -C ₄ -haloalkyl, _1, 2 or selected from C ₁ -C ₄ -alkoxy, C ₁ -C ₄ -alkylthio, C ₁ -C ₄ -haloalkoxy, C ₁ -C ₄ -haloalkylthio, cyano, nitro, phenoxy and pyridyloxy Substituted with 3 groups, where the last 2 groups listed here are unsubstituted or halogen, C ₁ -C ₄ -alkyl, C ₁ -C ₄ -haloalkyl, C ₁ -C Substituted with 1, 2 or 3 groups selected from ₄ -alkoxy, C ₁ -C ₄ -haloalkoxy, cyano and nitro,
A is a covalent bond or CH ₂ ,
5. A mixture according to any one of claims 1 to 4, comprising a compound of formula I or a salt thereof. R ¹ is phenyl, 3-chlorophenyl, 4-chlorophenyl, 3-fluorophenyl, 4-fluorophenyl, 4-methoxyphenyl, 3,4-dichlorophenyl, 3,5-dichlorophenyl, 2,5-dichlorophenyl, 3,4- Difluorophenyl, 3,5-difluorophenyl, 2,5-difluorophenyl, benzothien-2-yl, 2-thienyl, 5-chloro-2-thienyl, 3-methyl-2-thienyl, 5-methyl-2-thienyl , 3-thienyl, 2-methyl-3-thienyl, 2-chloro-3-thienyl or 4-methyl-3-thienyl,
Ar is phenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 2,4-dichlorophenyl, 2,3-dichlorophenyl, 3,4-dichlorophenyl, 2 , 6-dichlorophenyl, 2-chloro-4-fluorophenyl, 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl, 2,4-difluorophenyl, 2,5-difluorophenyl, 3,5-difluorophenyl, 3,4-difluorophenyl, 3-chloro-4-fluorophenyl, 4-chloro-2-fluorophenyl, 2-chloro-5-trifluoromethylphenyl, 2-fluoro-4-trifluoromethylphenyl, 2-fluoro -5-trifluoromethylphenyl, 3-fluoro-5-trifluoromethylphenyl, 2-chloro-3-trifluoromethylphenyl, 4-fluoro-3-trifluoromethylphenyl, 4-methyl B-3-trifluoromethylphenyl, 3-chloro-4-methylphenyl, 2-trifluoromethylphenyl, 3-trifluoromethylphenyl, 4-trifluoromethylphenyl, 3-methoxyphenyl, 4-methoxyphenyl, 3 -Trifluoromethoxyphenyl, 4-trifluoromethoxyphenyl, 4-chloro-3,5-dimethylphenyl, 4-bromo-2,6-dimethylphenyl, 4- (4-chlorophenoxy) phenyl, 4-phenoxyphenyl, 3- (5-chloropyridin-2-yl) oxyphenyl, 3- (5-trifluoromethylpyridin-2-yl) oxyphenyl, 4- (5-chloropyridin-2-yl) oxyphenyl, 4- ( 5-trifluoromethylpyridin-2-yl) oxyphenyl, 3- (2-chloro-6-fluoro-4-trifluoromethylphenoxy) phenyl, 4- (2-chloro-6-fluoro-4-trifluoromethyl) Phenoxy) phenyl, 3- (2,6- Chloro-4-trifluoromethylphenoxy) phenyl, 4- (2,6-dichloro-4-trifluoromethylphenoxy) phenyl, are selected from 2,3,4,5-tetrafluorophenyl and pentafluorophenyl,
A is CH ₂
5. A mixture according to any one of claims 1 to 4, comprising a compound of formula I or a salt thereof. The following compounds:
2- [hydroxyl (pyridin-3-yl) methyl] acrylic acid (3-trifluoromethylphenyl) methyl;
2- [hydroxyl (pyridin-3-yl) methyl] acrylic acid (4-trifluoromethylphenyl) methyl;
2- [hydroxyl (pyridin-3-yl) methyl] -3-phenylacrylic acid (3-trifluoromethylphenyl) methyl;
2- [hydroxyl (pyridin-3-yl) methyl] -3-phenylacrylic acid (4-chloro-3-trifluoromethylphenyl) methyl;
2- [hydroxyl (pyridin-3-yl) methyl] -3- (4-chlorophenyl) acrylic acid (3-trifluoromethylphenyl) methyl;
2- [hydroxyl (pyridin-3-yl) methyl] -3- (2-chlorophenyl) acrylic acid (3-trifluoromethylphenyl) methyl;
2- [hydroxyl (pyridin-3-yl) methyl] -3- (3-chlorophenyl) acrylic acid (3-trifluoromethylphenyl) methyl;
2- [hydroxyl (pyridin-3-yl) methyl] -3- (4-fluorophenyl) acrylic acid (3-trifluoromethylphenyl) methyl;
2- [hydroxyl (pyridin-3-yl) methyl] -3- (2-fluorophenyl) acrylic acid (3-trifluoromethylphenyl) methyl;
2- [hydroxyl (pyridin-3-yl) methyl] -3- (3-fluorophenyl) acrylic acid (3-trifluoromethylphenyl) methyl;
2- [hydroxyl (pyridin-3-yl) methyl] -3- (3,4-difluorophenyl) acrylic acid (3-trifluoromethylphenyl) methyl;
2- [hydroxyl (pyridin-3-yl) methyl] -3- (3,5-difluorophenyl) acrylic acid (3-trifluoromethylphenyl) methyl;
2- [hydroxyl (pyridin-3-yl) methyl] -3- (2,5-difluorophenyl) acrylic acid (3-trifluoromethylphenyl) methyl;
2- [hydroxyl (pyridin-3-yl) methyl] -3- (3,4-dichlorophenyl) acrylic acid (3-trifluoromethylphenyl) methyl;
2- [hydroxyl (pyridin-3-yl) methyl] -3- (3,5-dichlorophenyl) acrylic acid (3-trifluoromethylphenyl) methyl;
2- [hydroxyl (pyridin-3-yl) methyl] -3- (2,5-dichlorophenyl) acrylic acid (3-trifluoromethylphenyl) methyl;
2- [hydroxyl (pyridin-3-yl) methyl] -3- (4-methoxyphenyl) acrylic acid (3-trifluoromethylphenyl) methyl;
2- [hydroxyl (pyridin-3-yl) methyl] -3- (3-thienyl) acrylic acid (3-trifluoromethylphenyl) methyl;
2- [hydroxyl (pyridin-3-yl) methyl] -3- (2-thienyl) acrylic acid (3-trifluoromethylphenyl) methyl;
2- [hydroxyl (pyridin-3-yl) methyl] -3- (5-chloro-2-thienyl) acrylic acid (3-trifluoromethylphenyl) methyl;
2- [hydroxyl (pyridin-3-yl) methyl] -3- (5-methyl-2-thienyl) acrylic acid (3-trifluoromethylphenyl) methyl;
2- [hydroxyl (pyridin-3-yl) methyl] -3- (3-methyl-2-thienyl) acrylic acid (3-trifluoromethylphenyl) methyl;
2- [hydroxyl (pyridin-3-yl) methyl] -3- (4-methyl-3-thienyl) acrylic acid (3-trifluoromethylphenyl) methyl;
2- [hydroxyl (pyridin-3-yl) methyl] -3- (5-methyl-3-thienyl) acrylic acid (3-trifluoromethylphenyl) methyl;
2- [hydroxyl (pyridin-3-yl) methyl] -3- (2-chloro-3-thienyl) acrylic acid (3-trifluoromethylphenyl) methyl;
2- [hydroxyl (pyridin-3-yl) methyl] acrylic acid 1- (3-trifluoromethylphenyl) propyl;
2- [hydroxyl (pyridin-3-yl) methyl] acrylic acid 2- (3-trifluoromethylphenyl) -1-methylethyl;
1- (3-trifluoromethylphenyl) ethyl 2- [hydroxyl (pyridin-3-yl) methyl] acrylate;
2- [hydroxyl (pyridin-3-yl) methyl] acrylic acid 2- (3-trifluoromethylphenyl) ethyl;
1- (2-phenylphenyl) ethyl 2- [hydroxyl (pyridin-3-yl) methyl] acrylate;
2- [hydroxyl (pyridin-3-yl) methyl] -acrylic acid (3-trifluoromethoxyphenyl) methyl;
2- [hydroxyl (pyridin-3-yl) methyl] -acrylic acid (4-trifluoromethoxyphenyl) methyl;
2- [hydroxyl (pyridin-3-yl) methyl] -acrylic acid (4-chloro-3-trifluoromethylphenyl) methyl;
2- [hydroxyl (pyridin-3-yl) methyl] -acrylic acid (3,4-dichlorophenyl) methyl;
2- [hydroxyl (pyridin-3-yl) methyl] -2- (4-chlorophenyl) ethyl acrylate;
2- [hydroxyl (pyridin-3-yl) methyl] -2- (3-chlorophenyl) ethyl acrylate;
2- [hydroxyl (pyridin-3-yl) methyl] -3- (3-thienyl) acrylic acid (2,6-dichlorophenyl) methyl;
2- [hydroxyl (pyridin-3-yl) methyl] -3- (3-thienyl) acrylic acid (2-chloro-3-trifluoromethylphenyl) methyl;
2- [hydroxyl (pyridin-3-yl) methyl] -3- (3-thienyl) acrylic acid (2-fluoro-3-trifluoromethylphenyl) methyl;
2- [hydroxyl (pyridin-3-yl) methyl] -3- (3-thienyl) acrylic acid (3-chloro-4-methylphenyl) methyl;
2- [hydroxyl (pyridin-3-yl) methyl] acrylic acid 4- (4-chlorophenoxy) phenylmethyl;
2- [hydroxyl (pyridin-3-yl) methyl] acrylic acid 4- (3-chlorophenoxy) phenylmethyl;
2- [hydroxyl (pyridin-3-yl) methyl] acrylic acid 4-phenoxyphenylmethyl;
2- [hydroxyl (pyridin-3-yl) methyl] acrylic acid 3- (5-chloropyridin-2-yloxy) phenylmethyl;
2- [hydroxyl (pyridin-3-yl) methyl] acrylic acid 4- (5-chloropyridin-2-yloxy) phenylmethyl;
2- [hydroxyl (pyridin-3-yl) methyl] acrylic acid 3- (5-trifluoromethylpyridin-2-yloxy) phenylmethyl;
2- [hydroxyl (pyridin-3-yl) methyl] acrylic acid 4- (5-trifluoromethylpyridin-2-yloxy) phenylmethyl;
2- [hydroxyl (pyridin-3-yl) methyl] acrylic acid 3- (2-chloro-6-fluoro-4-trifluoromethylphenoxy) phenylmethyl;
2- [hydroxyl (pyridin-3-yl) methyl] acrylic acid 4- (2-chloro-6-fluoro-4-trifluoromethylphenoxy) phenylmethyl;
2- [hydroxyl (pyridin-3-yl) methyl] acrylic acid 3- (2,6-dichloro-4-trifluoromethylphenoxy) phenylmethyl;
2- [hydroxyl (pyridin-3-yl) methyl] acrylic acid 4- (2,6-dichloro-4-trifluoromethylphenoxy) phenylmethyl;
2- [hydroxyl (pyridin-3-yl) methyl] acrylic acid 4-chlorophenyl;
2- [hydroxyl (pyridin-3-yl) methyl] acrylic acid 3-chlorophenyl;
2- [hydroxyl (pyridin-3-yl) methyl] acrylic acid 2-chlorophenyl;
2- [hydroxyl (pyridin-3-yl) methyl] acrylic acid 4-fluorophenyl;
2- [hydroxyl (pyridin-3-yl) methyl] acrylic acid 3-trifluoromethylphenyl;
2- [hydroxyl (pyridin-3-yl) methyl] acrylic acid 2,3-dichlorophenyl;
2- [hydroxyl (pyridin-3-yl) methyl] acrylic acid 2,4-dichlorophenyl;
2- [hydroxyl (pyridin-3-yl) methyl] acrylic acid 2,6-dichlorophenyl;
2- [hydroxyl (pyridin-3-yl) methyl] acrylic acid 3,4-dichlorophenyl;
2- [hydroxyl (pyridin-3-yl) methyl] acrylic acid 2,3-difluorophenyl;
2- [hydroxyl (pyridin-3-yl) methyl] acrylic acid 2,4-difluorophenyl;
2- [hydroxyl (pyridin-3-yl) methyl] acrylic acid 3,4-difluorophenyl;
2- [hydroxyl (pyridin-3-yl) methyl] acrylic acid 2,6-difluorophenyl;
2- [hydroxyl (pyridin-3-yl) methyl] acrylic acid 2,5-difluorophenyl;
2- [hydroxyl (pyridin-3-yl) methyl] acrylic acid 4-chloro-3-fluorophenyl;
2- [hydroxyl (pyridin-3-yl) methyl] acrylic acid 4-chloro-2-fluorophenyl;
2- [hydroxyl (pyridin-3-yl) methyl] acrylic acid 4-methoxyphenyl;
2- [hydroxyl (pyridin-3-yl) methyl] acrylic acid 4-phenoxyphenyl;
2- [hydroxyl (pyridin-3-yl) methyl] acrylic acid 4-methylphenyl;
2- [hydroxyl (pyridin-3-yl) methyl] acrylic acid 3- (5-chloropyridin-2-yloxy) phenylmethyl;
2- [hydroxyl (pyridin-3-yl) methyl] acrylic acid 3- (5-trifluoromethylpyridin-2-yloxy) phenylmethyl; and
2- [hydroxyl (pyridin-3-yl) methyl] acrylic acid 4- (5-trifluoromethylpyridin-2-yloxy) phenylmethyl;
12. A mixture according to any one of claims 1 to 11, comprising a compound of formula I selected from the group consisting of: The following compounds:
2- [hydroxyl (pyridin-3-yl) methyl] acrylic acid (3-trifluoromethylphenyl) methyl;
2- [hydroxyl (pyridin-3-yl) methyl] -3-phenylacrylic acid (3-trifluoromethylphenyl) methyl;
13. A mixture according to any one of claims 1 to 12, comprising a compound of formula I selected from the group consisting of and salts thereof.   The compound II comprising an active compound selected from carbendazim, cyazofamide, epoxiconazole, fluquinconazole, metconazole, propiconazole, prothioconazole, tebuconazole, triticonazole and prochloraz. The mixture according to item 1.   Compound II comprises an active compound selected from azoxystrobin, trifloxystrobin, cresoxime-methyl, dimoxystrobin, orisatrobin, picoxystrobin, pyraclostrobin, enestrobrin and methinostrobin Item 14. The mixture according to any one of Items 1 to 13.   14. A mixture according to any one of claims 1 to 13, comprising as the compound II an active compound selected from boscalid, metalaxyl, metalaxyl-M and dimethomorph.   14. A mixture according to any one of claims 1 to 13, comprising as the compound II an active compound selected from captan, cyprodinyl, pyrimethanil, fenpropimorph, tridemorph, fenpropidine and iprodione.   Compound 1 comprising an active compound selected from mancozeb, maneb, metam, methylam, thiram, thiophanate-methyl, fullbenchavaricarb (benchavaricarb), propineb and iprovalicarb. The mixture according to item.   14. A mixture according to any one of claims 1 to 13, comprising as the compound II an active compound selected from dodin, dithianone, fosetyl-aluminum, phosphorous acid and its salts, chlorothalonil, metolaphenone and spiroxamine.   14. Mixture according to any one of claims 1 to 13, comprising as the compound II an active compound selected from boscalid, propineb, captan, epoxiconazole, benchavaricarb, iprovaricarb, cyazofamid, pyrimethanil and pyraclostrobin. .   21. The mixture according to any one of claims 1 to 20, further comprising an insecticidal compound.   22. A mixture according to claim 21, wherein the insecticidal compound is selected from pyrethroids, in particular α-cypermethrin, and nicotine receptor agonist / antagonist compounds, in particular acetamiprid, clothianidin, dinotefuran, imidacloprid, thiamethoxam, nitenpyram and thiacloprid.   23. A mixture according to any one of claims 1-22, comprising compound I and compound II in a weight ratio of 100: 1 to 1: 100.   24. A bactericidal composition comprising a liquid or solid carrier and at least two bactericidal active ingredients, wherein the at least two bactericidal active ingredients are mixtures according to any one of claims 1 to 23. The sterilizing composition.   Treating a harmful phytopathogenic fungus, its habitat or a plant, soil or seed to be protected from attack by said pathogenic fungus with an effective amount of a mixture according to any one of claims 1 to 23. A method for controlling harmful plant pathogenic fungi.   26. The method according to claim 25, wherein the mixture according to any one of claims 1 to 23 is applied in an amount of 5 g / ha to 2000 g / ha.   27. A method according to claim 25 or 26, wherein compound I and compound II as defined in any of claims 1 to 23 are applied simultaneously, i.e. together or separately or sequentially.   24. A method of protecting a seed comprising contacting the seed with a bactericidal effective amount of the mixture of any one of claims 1-23.   30. A method according to claim 28, wherein the mixture according to any one of claims 1 to 23 is applied in an amount of 0.01 g to 10 kg per 100 kg of seeds.   24. A seed comprising the mixture according to any one of claims 1 to 23 in an amount of 0.1 g to 10 kg per 100 kg of seed.